반응 #72515

반응 방정식

N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide

ammonium chloride

→

2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide

수율 72.6%

용매

ethyl acetate

methanol

반응 조건

후처리

1. 1
   여과then filtered
2. 2
   농축concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe crude product was dissolved
4. 4
   온도in refluxing methanol (350 mL)
5. 5
   온도then cooled to room temperature
6. 6
   workup.ADDITIONtreated with water (300 mL)
7. 7
   기타to give a white precipitate which
8. 8
   여과was filtered
9. 9
   세척washed with water (50 mL)
10. 10
    기타dried under high vacuum at 60° C.

실험 절차

A solution of N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide (5.07 g, 17.38 mmol), ammonium chloride (5.30 g, 99.1 mmol) in methanol (170 mL) was treated with zinc dust (8.1 g, 123.9 mmol) and stirred for 1 hour at room temperature. The mixture was diluted with ethyl acetate (300 mL) then filtered and concentrated under reduced pressure. The crude product was dissolved in refluxing methanol (350 mL) then cooled to room temperature and treated with water (300 mL) to give a white precipitate which was filtered, washed with water (50 mL) and dried under high vacuum at 60° C. to give 2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide (3.3 g). M.p.=187-190° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.87 (s, 1H), 8.25 (dd, J=2.0, 4.8 Hz, 1H), 8.02 (dd, J=2.0, 8.0 Hz, 1H), 7.52 (s, 1H), 7.45 (dd, J=4.8, 8.0 Hz, 1H), 7.04 (dd, J=2.0, 8.8 Hz, 2H), 6.67 (d, J=8.4 Hz, 1H), 6.21 (s, 2H), 2.19 (s, 3H); LCMS [M+H]: 262.

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