Ammonium Chloride → (5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

HRID 1012610

反応式

HRID 1012610 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=1[CH3:28])=[O:18].[NH4+].[Cl-]>CO.[Zn]>[NH2:25][C:23]1[CH:22]=[CH:21][C:20]([CH3:28])=[C:19]([C:17]([C:3]2[CH:4]=[CH:5][C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])=[CH:7][C:2]=2[Cl:1])=[O:18])[CH:24]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 11618303[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

生成物 1

HCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

Compound 493 (6.0 g, 14.9 mmol) was dissolved in MeOH (350 mL). Zinc-dust (12.69 g, 194 mmol) and NH4Cl (5.59 g, 104 mmol) were added. The reaction mixture was heated at reflux temperature for 1 h. The mixture was filtered and washed with MeOH. The filtrate was concentrated and the solid was dissolved in EtOAc (150 mL) and saturated aqueous Na2CO3 (100 mL). The water phase was extracted with EtOAc and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:2 as the eluent to afford the title compound as a slightly coloured crystalline compound.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 1 h
  3. filtrationThe mixture was filtered
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe solid was dissolved in EtOAc (150 mL)
  7. extractionThe water phase was extracted with EtOAc
  8. dry with materialthe combined organic phases were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-960b8320cb0d4079b11a85a06b82281a
出典データセット
uspto-grants-2011_07
特許番号
US07977387B2

関連ノート

読み込み中…