Methyl 4-fluoro-5-methyl-2-nitrobenzoate → Methyl 2-amino-4-fluoro-5-methylbenzoate

HRID 1750851Notes

Reaction equation

HRID 1750851 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:13]([O-])=O)[CH:3]=1>CO.[Pd]>[NH2:13][C:4]1[CH:3]=[C:2]([F:1])[C:11]([CH3:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 58115689Methyl 4-fluoro-5-methyl-2-nitrobenzoate

Product 1

HCID 58115582Methyl 2-amino-4-fluoro-5-methylbenzoateYield 51.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of crude methyl 4-fluoro-5-methyl-2-nitrobenzoate (5 g) in MeOH (50 mL) was hydrogenated using 10% Pd/C (0.5 g) as catalyst at atmospheric pressure overnight. The catalyst was removed by filtration, and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (8:1) to give methyl 2-amino-4-fluoro-5-methylbenzoate (2.21 g, yield 50% over three steps) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.715 (d, J=9.0 Hz, 1H), 6.339 (d, J=11.5 Hz, 1H), 3.873 (s, 3H), 2.154 (s, 3H) ppm.

Workup

  1. customat atmospheric pressure overnight
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated at reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with PE-EA (8:1)

Sources & evidence

ORD record
ord-b1168a31c78a409bb3f249486351fcda
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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