5-Methyl-2-nitrobenzoic acid → 2-Amino-5-methylbenzoic acid

HRID 346582

Reaction equation

HRID 346582 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>C(O)C.[Pd]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 183715-Methyl-2-nitrobenzoic acid

Product 1

HCID 762552-Amino-5-methylbenzoic acidYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-2-nitrobenzoic acid (20 g, 110 mmol) in ethanol was added 10% Pd/C (1 g). The mixture was stirred overnight at room temperature under hydrogen atmosphere. The solution was filtered through celite and evaporated under reduced pressure to yield 16 g (96%) of white solids. M.P. 162° C. 1H NR (DMSO-d6): δ 2.13 (s, 3H), 6.65 (d, J=8.6 Hz, 1H), 7.06 (dd, J=8.6, 1.8 Hz, 1H), 7.48 (d, J=1.1, 1H). EIMS m/z 174 (M+1), 152 (M+23).

Workup

  1. filtrationThe solution was filtered through celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4d462a567b8c47b09f83dd84170cd1e5
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Linked notes

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