Methyl 2-fluoro-4-nitrobenzoate → Methyl 4-amino-2-fluorobenzoate

HRID 2080663Notes

Reaction equation

HRID 2080663 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H][H]>CO.O1CCCC1.[Ni]>[NH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

6

Reactant 2

HCID 3013872Methyl 2-fluoro-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 21957875Methyl 4-amino-2-fluorobenzoateYield 99.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

141 g of methyl 2-fluoro-4-nitrobenzoate was dissolved in 1000 ml of methanol and 400 ml of tetrahydrofuran, 20 g of Raney nickel was added to it, and stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration, and the solvent was evaporated away under reduced pressure to obtain 119 g of methyl 4-amino-2-fluorobenzoate.

Workup

  1. customThe catalyst was removed through filtration
  2. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-8900922c73de4645bf6e5999abfe58b4
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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