5-(Dimethylamino)-2-nitrobenzoic acid → 2-Amino-5-(dimethylamino)benzoic acid

HRID 596607Notes

Reaction equation

HRID 596607 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.[H][H]>[Ni].CC(N(C)C)=O.CO>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 127157935-(Dimethylamino)-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 127157942-Amino-5-(dimethylamino)benzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 17933507HCID 17933507, compoundSolvent

Procedure

A mixture of 18 g. of 2-nitro-5-dimethylaminobenzoic acid, 1.0 liter of a 50:50 mixture of dimethylacetamide/methanol and 18 g. of Raney Nickel is hydrogenated at a hydrogen pressure of 40-50 psi for 2 hours. The resulting mixture is filtered, washed with methanol and the total filtrate evaporated to a solid which is broken up, washed with ether and dried to obtain 2-amino-5-dimethylaminobenzoic acid, m.p. 231°-234° C. (decomp.).

Workup

  1. additionA mixture of 18 g
  2. filtrationThe resulting mixture is filtered
  3. washwashed with methanol
  4. customthe total filtrate evaporated to a solid which
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-b028b26a755046cbb69b862a0a1d716f
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Reaction notes

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