Methyl 4-fluoro-2-methyl-3-nitrobenzoate → Methyl 3-amino-4-fluoro-2-methylbenzoate

HRID 1639802Notes

Reaction equation

HRID 1639802 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-])=O>CO.[C].[Pd]>[NH2:13][C:3]1[C:4]([CH3:12])=[C:5]([CH:10]=[CH:11][C:2]=1[F:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 58575232Methyl 4-fluoro-2-methyl-3-nitrobenzoate

Product 1

HCID 59334547Methyl 3-amino-4-fluoro-2-methylbenzoateYield 42%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of a crudely purified product (6.00 g, purity 50%) of methyl 4-fluoro-2-methyl-3-nitrobenzoate and wet palladium carbon (10 wt %, 300 mg, 2.81 mmol) in methanol (100 mL) was stirred under hydrogen atmosphere for 4 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=1/20→1/10) to give the title compound (2.13 g, yield 42%).

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=1/20→1/10)

Sources & evidence

ORD record
ord-19a2b6f81e7944fc8b61e6221ea939f8
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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