Ammonium Chloride → 2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide

HRID 44237

반응식

HRID 44237 반응식
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>CO.C(OCC)(=O)C.[Zn]>[NH2:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[C:9]([NH:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:20]

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 3440161N-(2-chloropyridin-3-yl)-5-methyl-2-nitrobenzamide

생성물 1

HCID 140754362-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide수율 72.6%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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.

후처리

  1. filtrationthen filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude product was dissolved
  4. temperaturein refluxing methanol (350 mL)
  5. temperaturethen cooled to room temperature
  6. additiontreated with water (300 mL)
  7. customto give a white precipitate which
  8. filtrationwas filtered
  9. washwashed with water (50 mL)
  10. customdried under high vacuum at 60° C.

출처 및 근거

ORD 기록
ord-baa8cf71640d4d32a2da16e6b83566db
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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