3-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acid → 3-Amino-4-phenoxy-5-sulfamoylbenzoic acid

HRID 979180Notes

Reaction equation

HRID 979180 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:20](=[O:23])(=[O:22])[NH2:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 1199263-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-nitro-4-phenoxy-5-sulfamoylbenzoic acid (3.7 g, 0.011 mol), 10% palladium on carbon (0.5 g) and ethanol (100 ml) is shaken on a Parr hydrogenator for 1.5 hours at a hydrogen pressure of 40 psi. The catalyst is filtered off and the filtrate is concentrated to yield 3-amino-4-phenoxy-5-sulfamoylbenzoic acid (IX-A).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c372593426ed4bd4a554efd568c632ab
Source dataset
uspto-grants-1987_05
Patent number
US04666906

Reaction notes

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