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

HRID 1012610

Reaktionsgleichung

Reaktionsgleichung von HRID 1012610
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-960b8320cb0d4079b11a85a06b82281a
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977387B2

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