Methyl 5-fluoro-2-methyl-3-nitrobenzoate → Methyl 3-amino-5-fluoro-2-methylbenzoate

HRID 887779Notes

Reaction equation

HRID 887779 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[C].[Pd]>[NH2:13][C:4]1[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([F:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 44203026Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Product 1

HCID 53419617Methyl 3-amino-5-fluoro-2-methylbenzoateYield 54%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 5-fluoro-2-methyl-3-nitrobenzoate (3.20 g, 15.0 mmol) in methanol (150 mL) was added palladium-carbon powder (320 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (1.47 g, yield 54%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d9bcf6d6c454a35a601fdf96a745dbd
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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