Methyl 6-fluoro-2-methyl-3-nitrobenzoate → Benzoic acid, 3-amino-6-fluoro-2-methyl-, methyl ester

HRID 1639775Notes

Reaction equation

HRID 1639775 reaction equation
[F:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1>CO.[C].[Pd]>[NH2:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 59334469Methyl 6-fluoro-2-methyl-3-nitrobenzoate

Product 1

HCID 59334575Benzoic acid, 3-amino-6-fluoro-2-methyl-, methyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of a crudely purified product (27.7 g, 130 mmol) of methyl 6-fluoro-2-methyl-3-nitrobenzoate in methanol (260 mL) was added palladium carbon (6.00 g, 10 wt %) and the mixture was stirred under hydrogen atmosphere for 12 hr. The catalyst was filtered off through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (15.0 g, yield 63%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-ea6640d6148146818e7881acfd430e9a
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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