3-Nitro-4-phenyl-5-sulfamylbenzoic acid → 3-Amino-4-phenyl-5-sulfamylbenzoic acid

HRID 1605575Notes

Reaction equation

HRID 1605575 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:19](=[O:22])(=[O:21])[NH2:20])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8])([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:19](=[O:22])(=[O:21])[NH2:20])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 215468433-Nitro-4-phenyl-5-sulfamylbenzoic acid

Product 1

HCID 215468413-Amino-4-phenyl-5-sulfamylbenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 23938PalladiumSolvent

Procedure

To a solution of 3-nitro-4-phenyl-5-sulfamylbenzoic acid (8.5 g) in acetic acid (100 ml), palladium (10%) on carbon (1.5 g) is added, and the mixture is hydrogenated. After 2-2.5 hours the theoretical amount of hydrogen has been absorbed, and the hydrogen uptake has subsided. The catalyst is removed by filtration, and the filtrate is evaporated in vacuo. The residue is recrystallized from acetic acid to give 3-amino-4-phenyl-5-sulfamylbenzoic acid with a melting point of 232.5°-237° C.

Workup

  1. customAfter 2-2.5 hours the theoretical amount of hydrogen has been absorbed
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated in vacuo
  4. customThe residue is recrystallized from acetic acid

Sources & evidence

ORD record
ord-8cf6a0da7ddb42d4960d7d943f93761f
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

Loading…