6-Methyl-2-nitrobenzoic acid → Methyl 2-methyl-6-nitrobenzoate

HRID 1814991Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][Si](C=[N+]=[N-])(C)C>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

Reactant 2

HCID 160976-Methyl-2-nitrobenzoic acid

HCID 167693Trimethylsilyldiazomethane

Product 1

HCID 596057Methyl 2-methyl-6-nitrobenzoate

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-444c06fc1f4a4906bcae1e0ee116f207
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878720B2

Reaction notes

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