Stearyl MethoxyPEGglycol Succinate a designer micellar medium for diverse aniline derivatives synthesis. Supporting information

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1 Electronic Supplementary Information (ESI) for: Stearyl MethoxyPEGglycol Succinate a designer micellar medium for diverse aniline derivatives synthesis Jagatheeswaran Kothandapani, Sengan Megarajan, Khan Behlol Ayaz Ahmed, Marimuthu Priyanka, Veerappan Anbazhagan* and Subramaniapillai Selva Ganesan* Department of Chemistry, School of Chemical and Biotechnology SASTRA University, Tirumalaisamudram, Thanjavur613401, Tamil Nadu, India Corresponding Author S.S.G: Department of Chemistry, School of Chemical and Biotechnology, SASTRA University, Tirumalaisamudram, Thanjavur , Tamil Nadu, India. Phone: ; Fax: selva@biotech.sastra.edu V.A: Department of Chemistry, School of Chemical and Biotechnology, SASTRA University, Tirumalaisamudram, Thanjavur , Tamil Nadu, India. Phone: ; Fax: , anbazhagan@scbt.sastra.edu Supporting information Total number of pages : 65 Total number of figures : 3 Total number of tables : 1 S. No Details Page No 1 Methods for the synthesis of SMPS and details of SMPS assisted synthesis of aniline derivatives S2-S8 2 Scanned copies of SMPS spectra S9-S15 3 Scanned copies of aniline derivatives spectra S16-S34 4 Scanned copies of aniline tethered indole spectra S35-S62 5 Toxicity studies of SMPS S63-S65 S 1

2 Materials and methods: Materials: Succinic acid, stearyl alcohol, p-toluene sulfonic acid, triethylamine and acetophenone derivatives were purchased from avra chemicals. Silic gel (code ) mesh size was purchased from Loba Chemie Pvt Ltd. Poly(ethylene glycol)methyl ether (Mn = 550; Product code G) was purchased from Aldrich. Indole, 4-nitro and 3-nitro benzaldehyde were purchased from Alfa Aeser. Ammonium chloride, zinc dust, N,N-dimethylaniline and aromatic aldehydes were purchased from Merck Pvt Ltd. Melting points were uncorrected. 1 H NMR was recorded Brucker model avance-ii 300 MHz and 13 C 75 MHz spectrometer using TMS as an internal standard and CDCl3 and DMSO-d6 as a solvent. 19 FNMR spectrum was recorded on a Varian Unity Plus 400 spectrometer (at Hz). The JEOL GCMATE II GC-MS with Data system is a high resolution, Electron impact (EI) methods were used for analyzing mass of molecules. FT-IR spectrum was taken Perkin Elmer Spectrum RX I model. Methods Synthesis of 4-(octadecyloxy)-4-oxobutanoic acid: A 100 ml round-bottom flask was charged with stearyl alcohol (5.4 g, 20 mmol), succinic anhydride (2.0 g, 20 mmol) and toluene (40 ml). To this well-stirred mixture, triethylamine (0.7 ml, 5 mmol) was added, and the reaction flask was placed in an oil bath at 60 C for 10 h. After completion of reaction, the toluene removed from the reaction mixture under reduced pressure. The crude reaction mixture was quenched by adding water (1 x 10 ml) and extracted dichloromethane (3 x 20 ml). The combined organic extracts were washed with water (1 x 10 ml) and dried over anhydrous Na2SO4 and concentrated under reduced pressure. 4-(octadecyloxy)-4-oxobutanoic acid : White solid, Yield : 6.0 g (81%), mp; C 1 H- NMR (300 MHz, CDCl3); δ 0.88 (t, J = 6.0 Hz, 3H), 1.25 (br s, 30H), (m, 2H), (m, 4H), 4.09 (t, J = 6.6 Hz, 2H). 13 C-NMR (75 MHz, CDCl3); δ 8.4, 14.1, 22.7, 25.8, 28.5, 28.9, 29.1, 29.3, 29.4, 29.5, 29.6, 29.7, 31.9, 45.3, 65.0, 172.3, IR(KBr): 3459, 2964,2920, 2840, 1734, 1685, 1471, 1310 cm -1 S 2

3 Synthesis of fatty acid surfactant (SMPS): The 4-(octadecyloxy)-4-oxobutanoic acid (1.29 g, 3.5 mmol), polyethylene glycol (Mn = 550) (3.19 g, 5.8 mmol), and p-toluenesulfonic acid (0.21 g, 1.2 mmol) were added into a 100 ml round-bottom flask. Toluene (40 ml) was added via syringe, and then the mixture was refluxed for 8 hours using a Dean Stark apparatus. After cooling to room temperature, the reaction mixture was quenched with water and extracted with dichloromethane (2 20 ml). The combined organic extracts were washed with brine (1 20 ml), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The product was obtained as viscous liquid. SMPS, Viscous liquid, Yield: 2.1 g (66%), 1 H-NMR (300 MHz, CDCl3): δ 0.88 (t, J = 6.9 Hz, 3H), 1.26 (br s, 28H), (m, 2H), (m, 5H), 3.38 (br s, 5H), (m, 4H), (m, 70H), 4.07 (t, J = 6.9 Hz, 2H) 4.24 (t, J = 5.1 Hz, 2H); 13 C-NMR (75 MHz, CDCl3); δ 22.5, 25.7, 28.4, 28.9, 29.0, 29.1, 29.2, 29.3, 29.4, 29.46, 29.52, 31.8, 58.8, 61.4, 63.7, 64.8, 68.9, 70.0, 70.3, 70.4, 71.7, 72.6, ESI-MS m/z = 936 [M+ Na] + IR (KBr): 2969, 2920, 2848, 2746, 2674, 2487, 1720, 1466 cm -1 General procedure for chemoselective reduction of acetophenone and chalcone derivatives (1a-j): 20 mg of surfactant was dispersed in 3 ml of water. To this nitrobenzene/nitroacetophenone/chalcone derivatives (0.25 mmol), zinc powder (0.5 g) and ammonium chloride (1 mmol, 60 mg) were added and the reaction mixture was stirred at room temperature for 3 hours. After completion of reaction, the reaction mixture was filtered, extracted with ethyl acetate (2 x 10 ml). The combined organic extracts were washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The product was purified by silica gel ( mesh size from Loba Chemie Pvt. Ltd.) column chromatography using ethyl acetate:hexane (1:3) as eluent. 3-(-4-Aminophenyl)-1-phenylpropan-1-one (1a). White gummy mass 1, yield: 46 mg (81%); 1 H-NMR (300 MHz, DMSO-d6): δ 2.76 (t, J = 7.5 Hz, 2H), 3.25 (t, J = 7.2 Hz, 2H), 4.83 (s, 2H), 6.47 (d, J = 8.1 Hz, 2H), 6.90 (d, J = 8.4 Hz, 2H), (m, 3H), 7.97 (d, J = 7.2 Hz, 2H). S 3

4 3-(-3-Aminophenyl)-1-phenylpropan-1-one (1b). White solid, yield: 44 mg (79%); mp C (64-65 C) 2 1 H-NMR (300 MHz, CDCl3): δ 2.97 (t, J = 7.2 Hz, 2H), 3.28 (t, J = 6.3 Hz, 2H), 3.65 (brs, 2H), (m, 1H), 6.59 (t, J = 1.5 Hz, 1H), 6.65 (d, J = 7.5 Hz, 1H), 7.09 (t, J = 7.8 Hz, 1H), (m, 2H), (m, 1H), (m, 2H). 3-(3-Aminophenyl)-1-(4-fluorophenyl)propan-1-one (1c). White solid, yield: 50 mg (83%);gummy mass, 1 H-NMR (300 MHz, DMSO-d6): δ 2.77 (t, J = 7.5 Hz, 2H), 3.29 (t, J = 7.5 Hz, 2H), 4.94 (s, 2H), (m, 3H), 6.91 (t, J = 7.8 Hz, 1H), 7.34 (t, J = 9.0 Hz, 2H), (m, 2H); 13 C-NMR (75 MHz, DMSO-d6); δ 30.1, 40.2(merged with DMSO-d6 peak), 112.2, 114.4, 115.9, , , 129.2, 131.3, 131.4, , , 142.1, 149.0, 163.7, 167.1, (Extra peaks were observed in the 13 C-NMR due to the fluorine-carbon coupling. The fluorine attached carbon showed a splitting of 250 Hz at ppm. The remaining carbon atoms of 4 fluorobenzaldehyde gave peaks with coupling constant 3 Hz, 5.25 Hz and 9 Hz at ppm, ppm and ppm respectively). 19 F-NMR (376 MHz, DMSO-d6) δ ppm. GC-MS m/z = calculated , found , IR(KBr): 3468, 3383, 3067, 2920, 2848, 1680, 1582, 1528, 1479 cm -1 3-(3-Aminophenyl)-1-(4-chlorophenyl)propan-1-one (1d). White solid, yield: 50 mg (77%); mp C, 1 H-NMR (300 MHz, CDCl3): δ (m, 2H), 3.24 (t, J = 6.6 Hz, 2H), 3.72 (brs, 2H), (m, 2H), 6.63 (d, J = 7.5 Hz, 1H), (m, 1H), (m, 2H), (m, 2H). 13 C-NMR (75 MHz, CDCl3); δ 30.2, 40.5, 113.9, 118.4, 119.6, 126.1, , , 129.5, 137.9, 141.4, 146.8, GC-MS m/z = calculated , found IR(KBr): 3446, 3372, 2928, 2845, 2328, 1690, 1570, 1458 cm -1 1-(3-aminophenyl)-3-phenylpropan-1-one (1e). White solid, yield: 42 mg (75%); mp C, 1 H-NMR (300 MHz, CDCl3): δ 3.04 (t, J = 7.5 Hz, 2H), 3.25 (t, J = 8.4 Hz, 2H), 3.80 (brs, 2H), 6.85 (ddd, J = 8.1, 2.7, 1.2 Hz, 1H), (m, 8H). 13 C-NMR (75 MHz, DMSO-d6); δ 30.1, 40.3(merged with DMSO-d6 peak), 113.1, 116.0, 118.9, 126.3, 128.7, 128.8, 129.5, 137.8, 141.8, 149.5, GC-MS m/z = calculated found IR(KBr): 3462, 3365, 3041, 2919, 1676, 1597, 1445, cm -1 1-(3-Aminophenyl)ethan-1-one (1g). White solid, yield: 30 mg (88%); mp C (96-97 C) 3 1 H-NMR (300 MHz, CDCl3): δ 2.56 (s, 3H), 3.65 (br s, 2H), 6.87 (ddd, J = 7.8, 2.4, 1.2 Hz, 1H), (m, 2H merged with CDCl3), 7.33 (dt, J = 7.8, 1.2 Hz, 1H). 1-(4-Aminophenyl)ethan-1-one (1h).Yellow oil 4, yield: 28 mg (85%); 1 H-NMR (300 MHz, CDCl3): δ 2.51 (s, 3H), 4.13 (brs, 2H), 6.65 (d, J = 6.9 Hz, 2H), 7.81 (d, J = 6.9 Hz, 2H) S 4

5 3-Benzoyl-4-chloroaniline (1i) 5. White solid, yield: 50 mg (87%); mp C, 1 H- NMR (300 MHz, CDCl3): δ 3.80 (brs, 2H), 6.65 (d, J = 2.7 Hz, 1H), 6.72 (dd, J = 8.7, 3.0 Hz, 1H), 7.19 (d, J = 8.4 Hz, 1H), (m, 2H), 7.59 (tt, J = 7.2, 1.5 Hz, 1H), (m, 2H). 4-Fluoroaniline (1j). Pale yellow liquid, yield: 24 mg (86%); 1 H-NMR (300 MHz, DMSOd6): δ 4.93 (s, 2H), (m, 2H), (m, 2H). General procedure for synthesis of amino bis(indolyl)methane derivatives (2,2a-h): To a stirred solution of nitobenzaldeyde (0.5 mmol) and substituted indole (1mmol) in 3 ml water, HCl (200 µl) was added and stirred at room temperature for 30 minutes. Then 20 mg surfactant and Zn dust (500 mg) were added and the solution was refluxed for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with water (10 ml) and extracted with ethyl acetate (1 20 ml). The crude reaction mixture was dried over anhydrous Na2SO4, concentrated under reduced pressure and the crude residue was purified by silica gel (60-200) column chromatography with ethyl acetate:hexane (2:3 v/v) as eluent. 4-[Bis(1H-indol-3-yl)methyl]aniline (2). White solid, yield: 137 mg (81%); mp C ( ) 6 1 H-NMR (300 MHz, DMSO-d6): δ 4.83 (s, 2H), 5.62 (s, 1H), 6.46 (d, J = 8.4 Hz, 2H), 6.76 (d, J = 1.8 Hz, 2H), 6.84 (t, J = 7.2 Hz, 2H), (m, 4H), 7.26 (d, J = 7.8 Hz, 2H), 7.32 (d, J = 8.1 Hz, 2H), (brs, 2H). 3-[Bis(5-methoxy-1H-indol-3-yl)methyl]aniline (2a). White solid, yield: 139 mg (70%); mp C 1 H-NMR (300 MHz, CDCl3): δ 3.68 (brs, 2H, merged with OMe protons), 3.69 (s, 6H), (m, 1H), (m, 3H), (m, 4H), 7.11 (d, J = 8.4 Hz, 1H), (m, 2H), 7.44 (dd, J = 8.7, 3.3 Hz, 1H), 7.80 (brs, 1H), 7.88 (d, J = 6.3 Hz, 1H), (m, 1H). 13 C-NMR (75 MHz, CDCl3 and DMSO-d6); δ 39.4 (CH peak merged with DMSO-D6 peak), 55.1, 100.7, 110.8, 111.6, 116.3, 120.5, 122.7, 124.3, 126.3, 128.4, 131.6, 134.4, 146.3, 147.6, GC-MS m/z = calculated found IR(KBr): 3521, 3419, 3000, 2933, 1711, 1613, 1573, 1479, 1207, 1163, 1038, 1016, 922 cm -1 S 5

6 3-[Bis(1H-indol-3-yl)methyl]aniline (2b). White solid, yield: 133 mg (79%); mp C ( C) 6 1 H-NMR (300 MHz, DMSO-d6): δ 4.83 (s, 2H), 5.61 (s, 1H), 6.46 (d, J = 8.4 Hz, 2H), 6.76 (s, 2H), 6.84 (t, J = 6.0 Hz, 2H), (m, 4H), 7.25 (d, J = 7.8 Hz, 2H), 7.32 (d, J = 8.1 Hz, 2H), (brs, 2H). 3-[Bis(1-methyl-1H-indol-3-yl)methyl]aniline (2c). White solid, yield: 139 mg (76%); mp C 1 H-NMR (300 MHz, CDCl3): δ 3.56 (brs, 2H), 3.67 (s, 6H), 5.77 (s, 1H), (m, 3H), 6.67 (br s, 1H), 6.77 (d, J = 7.8 Hz, 1H), 7.00 (t, J = 7.2 Hz, 2H), 7.07 (t, J = 7.8 Hz, 1H), 7.19 (t, J = 7.2 Hz, 2H), (m, 2H merged with CDCl3 peak), (m, 2H). 13 C-NMR (75 MHz, CDCl3); δ 32.6, 39.2, 108.9, 115.1, 118.5, 118.8, 120.1, 121.3, 127.5, 128.1, 129.4, 134.8, 137.4, GC-MS m/z = calculated found (M+1). IR(KBr): 3401, 3326, 3182, 3053, 2915, 2843, 1720, 1613 cm -1 4-[Bis(5-bromo-1H-indol-3-yl)methyl]aniline (2d). White solid, yield: 172 mg (70%); mp C 1 H-NMR (300 MHz, DMSO-d6): δ 4.88 (s, 2H), 5.62 (s, 1H), 6.49 (d, J = 8.4 Hz 2H), 6.82 (d, J = 1.8 Hz, 2H), 6.97 (d, J = 8.4 Hz, 2H), 7.14 (dd, J = 8.7, 2.1 Hz, 2H), 7.32 (d, J = 8.7 Hz, 2H), 7.39 (d, J = 1.8. Hz, 2H), (s, 2H). 13 C-NMR (75 MHz, CDCl3 and DMSO-d6); δ (CH peak merged with DMSO-d6 peak ) 110.8, 116.4, 118.1, 118.5, 120.8, 122.6, 123.4, 125.9, 128.8, 136.2, 145.5, GC-MS m/z = calculated found IR(KBr): 3411, 2919, 2847, 2346, 1605, 1453cm -1 4-[Bis(2-methyl-1H-indol-3-yl)methyl]aniline (2e) 7. Pale white gummy mass, yield: 146 mg (80%); 1 H-NMR (300 MHz, CDCl3 and a drop of DMSO-d6 was added to enhance the solubility): δ 2.07 (s, 6H), 3.75 (brs, 2H), 5.87 (s, 1H), 6.58 (d, J = 6.6 Hz, 2H), 6.78 (t, J = 8.1 Hz, 2H), (m, 6H), 7.23 (d, J = 7.8 Hz, 2H), 8.84 (s, 2H). 4-[Bis(1-methyl-1H-indol-3-yl)methyl]aniline (2f); White solid, yield: 148 mg (81%), mp C 1 H-NMR (300 MHz, CDCl3, δ ppm): 3.57 (brs, 2H), 3.67 (s, 6H), 5.77 (s, 1H), 6.51 (s 2H), 6.61 (d, J = 7.8 Hz, 2H), 6.98 (td, J = 6.9, 0.9 Hz, 2H), 7.10 (d, J = 7.8 Hz, 2H), 7.17 (td, J = 8.1, 1.2 Hz, 2H), (m, 2H merged with CDCl3), 7.39 (d, J = 7.8 Hz, 2H). 13 C-NMR (75 MHz, CDCl3 and DMSO-d6); 31.9, (CH peak merged with DMSOd6 peak) 108.3, 112.0, 114.4, 117.3, 117.7, 119.0, 120.5, 126.6, 127.3, 128.1, 136.5, 144.8, GC-MS m/z = calculated found IR(KBr): 3401, 3321, 3205, 3169, 3053, 2910, 1733, 1622, 1515, 1461 cm -1 S 6

7 3-[Bis(5-bromo-1H-indol-3-yl)methyl]aniline (2g). White solid, yield: 182 mg (74%); mp C 1 H-NMR (300 MHz, CDCl3): δ 3.59 (brs, 2H), 5.64 (s, 1H), (m, 2H), 6.66 (d, J = 1.5 Hz, 2H), 6.70 (d, J = 7.5 Hz, 1H), 7.08 (t, J = 7.8 Hz, 1H ), (m, 4H merged with CDCl3 peak), 7.49 (s, 2H), 7.98 (brs, 2H). 13 C-NMR (75 MHz, CDCl3); δ 39.7, 112.6, 112.6,113.6, 115.6, 118.8, 119.3, 122.2, , , 129.6, 135.3, 144.5, GC-MS m/z = calculated found , IR(KBr): 3407, 2925, 2848, 2348, 1609, 1454 cm -1 4-[Bis(5-methoxy-1H-indol-3-yl)methyl]aniline (2h). White solid, yield: 143 mg (72%); mp 186 C 1 H-NMR (300 MHz, CDCl3): δ 3.56 (brs, 2H), 3.70 (s, 6H), 5.67 (s, 1H), 6.54 (dd, J = 7.8, 1.2 Hz, 1H), (m, 3H), (m, 5H),7.07 (t, J = 7.8 Hz, 1H), (m, 2H merged with CDCl3 peak), 7.82 (brs, 2H). 13 C-NMR (75 MHz, CDCl3); δ 40.2, 55.9, 101.7, 112.0, 112.1, 117.6, 123.6, 124.6, 127.1, 129.5, 131.9, 146.5, 151.9, GC-MS m/z = calculated found (M+1). IR(KBr): 3513, 3422, 3003, 2938, 2829, 1708, 1619, 1510, 1482, 1208, 1174, 1044, 808 cm -1 General procedure for synthesis of diarylmethyl indoles (3): 20 mg of surfactant was dispersed in 1.5 ml of water. To this indole (1 mmol, 117 mg), benzaldehyde (1mmol, 106 mg), N,N dimethylaniline (1mmol, 126 µl), zinc chloride (0.5 mmol, 68 mg) added and stirred at room temperature for 6 h, reaction completion monitored by TLC. The reaction mixture diluted with 10 ml of water extracted with ethyl acetate (2 x 20 ml). The combined organic extracts were washed with water and dried with anhydrous Na2SO4, concentrated under reduced pressure and purified by silica gel column chromatography. 4-[1H-Indol-3-yl(phenyl)methyl]-N,N-dimethylaniline (3). White solid, yield: 248 mg (76%); mp C ( o C) 8 1 H-NMR (300 MHz, CDCl3): δ 2.91 (s, 6H), 5.58 (s, 1H), 6.58 (s, 1H), 6.67 (d, J = 8.7 Hz, 2H), 6.97 (t, J = 7.2 Hz, 1H), 7.09 (d, J = 8.7 Hz, 2H), (m, 8H), 7.34 (d, J = 8.1 Hz, 1H), 7.92 (s, 1H). S 7

8 References 1 Dasgupta, A.; Ramkumar, V.; Sankararaman, S. RSC Adv., 2015, 5, Adams, R.; Cohen, F. L.; Rees, O. W. J. Am. Chem. Soc., 1927, 49, Tibhe, J.; Sharma, Y.; Joshi, R. A.; Joshi, R. R.; Kulkarni, A. A. Green Process Synth., 2014, 3, Mori, A.; Mizusaki, T.; Kawase, M.; Maegawa, T.; Monguchi, Y.; Takao, S.; Takagi, Y.; Sajiki, H. Adv. Synth. Catal., 2008, 350, Zhang, F.; Li, N.; Zhang. S. J. Appl. Pol. Sci., 2010, 118, Imran, S.; Taha, M.; Ismail, N. H.; Fayyaz, S.; Khan, K. M.; Choudhary, M. I. Bioorganic Chemistry, 2015, 62, National Center for Biotechnology Information. PubChem Compound Database; CID=345520, (accessed Jan. 3, 2017). 8. Liu, J.; He, T.; Wang, L. Tetrahedron 2011, 67, S 8

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63 (A) (B) (C) (D) (E) (F) seed growth (cm) SMPS (mg/ml) Fig. S1: Phytotoxicity assessment from seed germination. Mung bean seeds are soaked for 2 h in different concentration of SMPS and then transferred to Petri plate and allowed to grow for 24 h in dark. The seed germination was measured using thread and scale. SMPS in (A) 0 mg/ml; (B) 5 mg/ml; (C) 10 mg/ml; (D) 20 mg/ml; (E) 40 mg/ml and (F) graph shows the root growth was unaltered at different concentration of SMPS, indicating the non-toxic nature of SMPS. S 63

64 Fig. S2: Bacteriotoxicity of SMPS. Zone of inhibition was evaluated by well diffusion method against Gram Negative bacteria, (A) Escherichia coli, (B) Pseudomonas aeruginosa and Gram positive bacterial (C) Bacillus subtils, (D) Staphylococcus aureus. 50 µl of SMPS was added to each well and the plates are incubated for 24 h at 37 o C. The concentrations of SMPS are (a) 5 mg/ml, (b) 10 mg/ml, (c) 20 mg/ml and (d) 40 mg/ml. No zone of inhibition was observed in both classes of bacteria, suggesting that SMPS would be safer for environmental friendly bacteria. S 64

65 SMPS SDS Triton X-100 Fig. S3: Bacteriotoxicity of SMPS, SDS and Triton X-100. Zone of inhibition (ZOI) was evaluated by well diffusion method against Escherichia coli. SDS and Triton X-100 showed ZOI, whereas no ZOI was observed for SMPS indicating its non-toxic nature. Each well is loaded with 50 µl of respective samples (40 mg/ml) and incubated at 37 o C for 24 h. Table S1: Aquatic toxicity. Mortality of zebra fish was evaluated using different concentration of SMPS. The described amount of SMPS was dissolved in tap water and allowed the fish to live in that environment. Group Group profile Total number of fishes Fishes alive after 48 h A No SMPS B 5 mg/ml SMPS C 10 mg/ml SMPS D 20 mg/ml SMPS E 40 mg/ml SMPS S 65