Hydrochloric Acid → (2-Amino-5-chloro-phenyl)-(2-methyl-pyridin-4-yl)-methanone

HRID 1497273ノート

反応式

HRID 1497273 の反応式
B(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][N:21]=1)[C:17]#N.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH-:27].[Na+]>ClC(Cl)C(Cl)Cl>[NH2:10][C:9]1[CH:11]=[CH:12][C:6]([Cl:5])=[CH:7][C:8]=1[C:17]([C:16]1[CH:19]=[CH:20][N:21]=[C:14]([CH3:13])[CH:15]=1)=[O:27]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) ChlorideHCID 119590732-Methylpyridine-4-carbonitrile

生成物 1

HCID 22327293(2-Amino-5-chloro-phenyl)-(2-methyl-pyridin-4-yl)-methanone収率 20%

試薬・触媒・溶媒 1

HCID 65911,1,2,2-Tetrachloroethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of boron trichloride (9.35 ml, 9.35 mmol) in 1,1,2,2-tetrachloroethane at 0° C. was added 4-chloroaniline (1.19 g, 9.35 mmol) and the mixture was stirred for 30 minutes. 2-methyl-isonicotinonitrile (920 mg, 7.79 mmol) and aluminum chloride (1.14 g, 8.57 mmol) were added successively and the mixture was heated to reflux for 20 h. The reaction mixture was cooled to 0° C., 2N HCl (20 ml) was added and the mixture was heated to 80° C. for 30 minutes. The mixture was basified with 3N NaOH and extracted with EtOAc. The combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5 to 100:0) to afford the title compound (390 mg, 20%) as yellow solid. MS (ESI): 247.4 (M+H)+.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 h
  3. temperaturethe mixture was heated to 80° C. for 30 minutes
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5 to 100:0)

出典と根拠

ORDレコード
ord-ca58c2d88f9a4540bcf3160a6c6e2199
出典データセット
uspto-grants-2015_12
特許番号
US09199938B2

反応ノート

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