Methyl 2-methyl-3-nitrobenzoate → 3-Amino-2-methylbenzoic acid methyl ester

HRID 962945Notes

Reaction equation

HRID 962945 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>[Pd].C(O)C>[CH3:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 38010253-Amino-2-methylbenzoic acid methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 2-methyl-3-nitrobenzoate (30 g, 154 mmol), 10% palladium on charcoal (3.0 g) and ethanol (350 mL) was shaken under hydrogen at 50 psig. After 4 h, the mixture was filtered through Celite® and the solids were washed with additional ethanol. The filtrate was concentrated to provide the title product (24.4 g, 96%) as a tan oil: 1H NMR (CDCl3) δ 7.18 (m, 1H), 7.06 (m, 1H), 6.78 (m, 1H), 3.85 (s, 3H), 2.34 (s, 3H); high resolution mass spectrum (NH3 --CI) calculated (M+H+) 166.0868, found 166.0866.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. washthe solids were washed with additional ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c6fa675e65c49a3aa0237f8ba58dbff
Source dataset
uspto-grants-1998_06
Patent number
US05760028

Reaction notes

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