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

HRID 650904Notes

Reaction equation

HRID 650904 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>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][CH:10]=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 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In the presence of 0.1 gram of 5% palladium on carbon, a solution of 14.0 grams (0.072 mole) of methyl 2-methyl-3-nitrobenzoate in 100 mL of ethanol was hydrogenated using a Parr hydrogenator, yielding 11.6 grams of subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was run several times.

Sources & evidence

ORD record
ord-86ece64ced9e465ea60bdbcfa40940b0
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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