2,5-dimethyl-3-nitrobenzoic acid → Benzoic acid, 3-amino-2,5-dimethyl-

HRID 259574Notes

Reaction equation

HRID 259574 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].NC1C(C)=C(C=CC=1C)C(O)=O>[Pd].CO>[NH2:11][C:10]1[C:2]([CH3:1])=[C:3]([CH:7]=[C:8]([CH3:14])[CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 2572572,5-dimethyl-3-nitrobenzoic acidHCID 22754770HCID 22754770, compound

Product 1

HCID 43471Benzoic acid, 3-amino-2,5-dimethyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,5-Dimethyl-3-nitrobenzoic acid (10.0 g.) was hydrogenated in 200 ml. of methanol in the presence of 0.5 g. of 5% palladium on carbon. The catalyst was removed on a filter and the filtrate was concentrated to dryness to give 8.3 g. of 3-amino-2,4-dimethylbenzoic acid, m.p. 145.5°-146.5° C.

Workup

  1. customThe catalyst was removed on
  2. filtrationa filter
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give 8.3 g

Sources & evidence

ORD record
ord-aa80e2321f354f44b67e1267e5ee2726
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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