Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides

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1 Supporting Information Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides Bin Feng, Yang Li, Huan Li, Xu Zhang, Huamei Xie, Hongen Cao, Lei Yu, and Qing Xu,, * College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang , P. R. China Institute of Pesticide of School of Chemistry and Chemical Engineering and School of Horticulture and Plant Protection, Yangzhou University, Yangzhou, Jiangsu , P. R. China qing-xu@wzu.edu.cn Table of Contents The Comparison and Differences of the N- and O-isomers 3a and 4a...S2 Solvent Evaluation during Condition Optimization..S5 Preliminary Mechanistic Studies S6 1 H and Spectra of the Products S11 S1

2 The Comparison and Differences of the N- and O-isomers 3a and 4a: The N-isomers (N-substituted pyridones) are in effect internal amide derivatives, polar and relatively high in melting points. The O-isomers (ethers) are usually much less polar oils. So they can be distinguished easily since they are greatly different in many aspects, such as the R f value in TLC analysis, the retention time and MS in GC-MS analysis under the same method, and also 1 H and spectra. 1. The difference in TLC analysis: As shown below, 3a is a rather polar molecule, but 4a is much less polar. 3a 4a 3a and 4a in the same plate (PE:EA=10:1) PE:EA =2:1 (3a need a much polar eluent) PE:EA=20:1 (4a need a much less polar eluent) 2. The difference in GC-MS spectra: GC-MS of 3a: (x1,000,000) TIC (1.00) S2

3 Ret. time: min, m/z = 185 % GC-MS of 4a: (x10,000,000) TIC Ret. time: min, m/z = % The difference in NMR spectra (see the characterization and NMR section for those of 3a): 4a 2-(Benzyloxy)pyridine (4a). Colorless oil. (500 MHz, CDCl 3 ): δ 8.18 (dd, J = 5.0 Hz, J = 1.0 Hz, 1H), (m, 1H), 7.46 (d, J = 7.5 Hz, 2H), (m, 2H), (m, 1H), (m, 1H), 6.80 (d, J = 8.5 Hz, 1H), 5.38 (s, 2H). (125.4 MHz, CDCl 3 ): δ 163.6, 146.8, 138.6, 137.4, 128.4, 127.9, 127.8, 116.9, 111.3, MS (EI): m/z (%) 185 (33), 184 (20), 108 (8), 92 (8), 91 (100), 80 (12), 79 (41), 65 (20), 52 (4), 51 (6). See ref. 17 in the manuscript for the preparation methods. S3

4 In a word, the N- and O-isomers are greatly different in many aspects. The simplest method to distinguish the N- and O-isomers is the use of eluent during the purification due to their different polarities. The N-isomers, product pyridones, usually require a much polar eluent like PE:EA =2:1. Some even require more polar eluent CH 2 Cl 2 :MeOH=10:1. S4

5 Solvent Evaluation during Condition Optimization: Entry Solvent (1 ml) 3a/4a GC 3a% isolated 1 Toluene >99/ EtOH >99/ DMF >99/ ,4-Dioxane >99/ THF >99/ MeOH >99/ DCE >99/ DCM >99/ CH 3 CN >99/1 59 Note: See Table 1 in the manuscript for standard conditions. S5

6 Preliminary Mechanistic Studies 1. Reaction of 2-Hydroxypyridine and Benzyl Bromide at a Lower Temperature (eq. 1 in the text). Procedure: The mixture of 2-hydroxypyridine 1a (190.0 mg, 2.0 mmol) and benzyl bromide 2a-Br (342.0 mg, 2.0 mmol, 1.0 equiv.) was sealed under air in a Schlenk tube (20 ml) and then stirred at 30 o C for 24 h. The reaction mixture was then analyzed by GC-MS (see below). GC spectra (~4% yield of 3a and 4a with a ratio of 22/78 was detected by GC): (x10,000) 9.0 TIC Ret. TM Start TM End TM m/z Area Area% Height Height% A/H Mark TIC MI TIC MI TIC MI MS spectra: Ret. time: min, m/z = 171, PhCH 2 Br (2a-Br) 1.0 (x10,000) 91 Br Ret. time: min, m/z = 185, N OCH 2 Ph (4a) % S6

7 Ret.time: min, m/z = 185, (3a) % Conversion of 2-Pyridyl Ether (4a) to N-Benzyl 2-Pyridone (3a) in the Presence of in situ Generated HBr (entry 1 of eq. 2 in the text). Procedure: To a 10 ml Schlenk tube was added 2-pyridyl benzyl ether 4a (194 mg, 1.04mmol), H 3 PO 4 (120mg, 1.04mmol) and NaBr(107mg, 1.04 mmol,). The mixture was then sealed under air and heated at 100 o C for 24 h, monitored by TLC/GC-MS, and purified by PTLC (preparative thin layer chromatography) using petroleum ether/etoac(2/1) as the eluent. Product 3a was obtained in 68% isolated yield as a white solid. GC-MS analysis of the reaction mixture showed that no 4a remained in the reaction mixture. So the selectivity of 3a is also >99%. This can account for the specific N-alkylation of the reaction. Instead, dibenzyl ether and 2-hydroxypyridine (1a) were observed as the byproducts. This revealed that some 4a is decomposed and may account for the moderate yield of 3a in the reaction. GC spectra: (x10,000,000) 2.0 TIC MS spectra: Ret. time: min, m/z = 92, S7

8 100.0 % Ret. time: min, m/z = 185, (3a) % Ret. time: min, m/z = 95, (1a) % Heating 2-Pyridyl Ether (4a) at 100 o C in the Absence of HBr (entry 2 of eq. 2 in the text). GC spectra: 1.25 (x10,000,000) TIC S8

9 MS spectra: Ret. time: min, m/z = 185, (4a) % As shown above, no reaction of 4a occurred at all in the absence of any acid. 4a was recovered in 87% yield. This result is consistent with the literature reports that the conversion of 4a to 3a requires a catalyst or a promoter (ref ). The result also clearly revealed the key role of HBr in the conversion of pyridyl ether intermediate 4 to product 3 that it may also be an active catalyst/promoter for the reaction in addition to the known catalysts or promoters (ref ). 4. GC-MS Analysis of the 12 h Reaction. The below results showed that, small amounts of the unreacted 1a and 2a were observed in addition to product 3a, but no 4a was observed at all. This revealed that the selectivity of 3a is indeed >99% even in the 12 h reaction. GC spectra: (x1,000,000) TIC (1.00) Enlarged GC spectra: (x100,000) TIC (1.00) MS spectra: S9

10 Ret. time: min, m/z = 185, (3a) % Ret. time: min, m/z = 95, (1a) % Ret. time: min, m/z = 169, (2a) % On the other hand, as shown by eq. 1 in the manuscript, we found 4a could only be detected at lower temperatures (such as room temperature) under the reaction conditions. In fact, 4a could quickly convert into 3a when heated at higher temperatures. These results may suggest that conversion of 1a and 2a to 4a is a kinetically fast process, while most likely due to the thermally unstable nature of 4a under the reaction conditions (or in the presence of HX), conversion of 4a to 3a is a thermodynamically favored process. Therefore, 4a was also not observed in the reaction of 12 h. S10

11 1 H and Spectra of the Products 3a S11

12 3b S12

13 3c S13

14 3d S14

15 3e S15

16 3f S16

17 3g S17

18 3h S18

19 3i S19

20 3j S20

21 3k S21

22 3l S22

23 3m S23

24 n-c 5 H 11 N O 3n S24

25 n-c 7 H 15 N O 3o S25

26 3p S26

27 3q S27

28 3r S28

29 3s S29

30 3t S30

31 3u S31

32 3v S32

33 6a S33

34 6b S34

35 6c S35

36 6d S36

37 6e S37

38 6f S38

39 6g S39

40 6h S40

41 6i S41

42 6j S42

43 6k S43

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