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

HRID 1279489Notes

Reaction equation

HRID 1279489 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 596057Methyl 2-methyl-6-nitrobenzoate

Product 1

HCID 583916Benzoic acid, 2-amino-6-methyl-, methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-6-nitrobenzoic acid is reacted with trimethylsilyldiazomethane to yield methyl 2-methyl-6-nitrobenzoate with m.p. 44-45° (Chem. Pharm. Bull., Vol. 29, 1475 (1981)). Methyl 2-methyl-6-nitrobenzoate is hydrogenated in methanol in the presence of palladium, 10% on carbon powder, at room temperature and atmospheric pressure to give methyl 2-methyl-6-aminobenzoate.

Sources & evidence

ORD record
ord-b3df42074a4c4b4cadd3da1e3506e480
Source dataset
uspto-grants-2002_09
Patent number
US06448277B2

Reaction notes

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