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

HRID 44237ノート

反応式

HRID 44237 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-baa8cf71640d4d32a2da16e6b83566db
出典データセット
uspto-grants-2013_09
特許番号
US08541407B2

反応ノート

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