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

HRID 1012610

반응식

HRID 1012610 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-960b8320cb0d4079b11a85a06b82281a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977387B2

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