Methyl 4-(1,1-difluoroethyl)-2-nitrobenzoate → Methyl 2-amino-4-(1,1-difluoroethyl)benzoate

HRID 1894111Notes

Reaction equation

HRID 1894111 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[CH3:11])=[CH:6][C:5]=1[N+:14]([O-])=O>CO.CCO.[Ni]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:12])([F:13])[CH3:11])=[CH:6][C:5]=1[NH2:14]

Participants

5

Reactant 1

HCID 59164516Methyl 4-(1,1-difluoroethyl)-2-nitrobenzoate

Product 1

HCID 59164446Methyl 2-amino-4-(1,1-difluoroethyl)benzoateYield 92.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 4-(1,1-difluoro-ethyl)-2-nitro-benzoic acid methyl ester (1.61 g, 6.57 mmol) in MeOH (40 mL) was treated with Nickel-raney in EtOH (400 mL) and the mixture was stirred at r.t. for 5 h under H2 (0.1 bar). The mixture was then filtered and concentrated in vacuo to give 2-amino-4-(1,1-difluoro-ethyl)-benzoic acid methyl ester (1.30 g, 6.05 mmol, 92%) as a yellow oil. ESI-MS: m/z 216 [M+H]+, rt 6.30 min.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d990fa5cd4c0496eb2ea7e083d52e09a
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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