3-Methyl-4-nitrobenzoic acid → 4-Amino-3-methylbenzoic acid

HRID 1695255Notes

Reaction equation

HRID 1695255 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)[C:5]([OH:7])=[O:6]>CN(C=O)C.[Ni]>[NH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 183703-Methyl-4-nitrobenzoic acid

Product 1

HCID 755984-Amino-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-methyl-4-nitro-benzoic acid (100 g, 0.55 mol) in DMF (500 mL), suspension of activated Raney Ni (50 g) in DMF (50 mL) was added and was subjected to hydrogenation (200 psi pressure and 25° C.) for 6 h. The reaction mixture was filtered through celite bed and was concentrated to one third of the total volume. The reaction mixture was poured into water (1300 mL) with stirring. The solid was filtered, washed with water and dried to obtain the title compound. Yield: 70 g (84%); 1H NMR (DMSO-d6, 300 MHz): δ 2.03 (s, 3H, CH3), 5.60 (s, 2H, NH2), 6.56 (d, 1H, Ar), 7.46 (d, 1H, Ar), 7.49 (s, 1H, Ar); MS: m/e (ES−) 150 (M−1).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite bed
  3. concentrationwas concentrated to one third of the total volume
  4. additionThe reaction mixture was poured into water (1300 mL)
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-18ee0747478844d68af0c50b8a967685
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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