3-Methyl-2-nitrobenzoic acid → 2-Amino-3-methylbenzoic acid

HRID 1520375Notes

Reaction equation

HRID 1520375 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]>[Pd].C1COCC1>[NH2:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 215753-Methyl-2-nitrobenzoic acid

Product 1

HCID 781012-Amino-3-methylbenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C catalyst (ISO mg) was suspended in a solution of 3-methyl-2-nitrobenzoic acid (1.50 g, 8.28 mmol, 1.0 eq) in THF (60 mL), the mixture was stirred under H2 atmosphere at room temperature overnight. The Pd/C was removed by filtration over Celite and the THF was removed in vacuo to give 1.23 g of Iv-a as a white solid (yield 98%). LCMS m/z=152.1 (M+1) (Method B) (retention time=0.73 min). The product was used further without purification.

Workup

  1. customThe Pd/C was removed by filtration over Celite
  2. customthe THF was removed in vacuo

Sources & evidence

ORD record
ord-f61f64f2f6e246b0bbecde2e7f766239
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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