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

HRID 260804Notes

Reaction equation

HRID 260804 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>CO.[Pt]=O>[NH2:11][C:10]1[C:2]([CH3:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 160962-Methyl-3-nitrobenzoic acid

Product 1

HCID 27336993-Amino-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-nitrobenzoic acid (mp. 182°-184° C., 22 g, 0.12 mol) in 400 mL of methanol was hydrogenated over platinum oxide (100 mg) for 45 minutes at 55 pounds per square inch (psi), whereupon the catalyst was filtered off through a bed of Celite® (50 g), and the solvent evaporated under reduced pressure to give 3-amino-2-methylbenzoic acid (mp. 178°-181° C.) in quantitative yield (18.3 g).

Workup

  1. filtrationwas filtered off through a bed of Celite® (50 g)
  2. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-14b48dccef744d71888c9ba77025118e
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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