Methanol → Tert-butyl 4-amino-2-(4-fluoroanilino)benzoate

HRID 2191625Notes

Reaction equation

HRID 2191625 reaction equation
CO.[F:3][C:4]1[CH:26]=[CH:25][C:7]([NH:8][C:9]2[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:10]=2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][CH:5]=1>[C].[Pd].C(OCC)(=O)C>[NH2:22][C:20]1[CH:19]=[CH:18][C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:9]([NH:8][C:7]2[CH:25]=[CH:26][C:4]([F:3])=[CH:5][CH:6]=2)[CH:21]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68965268Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

Product 1

HCID 68958505Tert-butyl 4-amino-2-(4-fluoroanilino)benzoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of methanol 5.0 mL and ethyl acetate 5.0 mL of tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate 1.0 g, was added 5% palladium-carbon 0.20 g, and it was stirred under hydrogen atmosphere at room temperature for 6 hours. Insoluble matter was filtrated, the solvent was removed under reduced pressure to give tert-butyl 4-amino-2-(4-fluoroanilino)benzoate 0.90 g of white solid.

Workup

  1. filtrationInsoluble matter was filtrated
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bae4fca4e37d473b9650afdd9580ad9d
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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