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

HRID 532231Notes

Reaction equation

HRID 532231 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-c5cfc5ae25e0433c8f239e798e8a162e
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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