Lithium Hydroxide → 3-Amino-4-phenoxy-5-sulfamoylbenzoic acid

HRID 918600Notes

Reaction equation

HRID 918600 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.[OH-].[Li+].[H][H]>O.[Pd]>[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

6

Reactant 3

HCID 3939Lithium HydroxideHCID 1199263-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 3-nitro-4-phenoxy-5-sulphamyl-benzoic acid (20 g) in water (100 ml) was adjusted to a pH of 8 by the addition of 1N lithium hydroxide. The resulting solution was hydrogenated at room temperature and 1.1 atmosphere hydrogen pressure, using a palladium-on-carbon catalyst (0.6 g catalyst containing 10% pd). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the 3-amino- 4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the filtrate by the addition of 4N hydrochloric acid until the pH was 2.5. After recrystallization from aqueous ethanol and drying, the melting point was 255°-256°C.

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. customthe 3-amino- 4-phenoxy-5-sulphamyl-benzoic acid was precipitated from the filtrate by the addition of 4N hydrochloric acid until the pH was 2.5
  4. customAfter recrystallization from aqueous ethanol
  5. customdrying

Sources & evidence

ORD record
ord-6e8efe1a28ff414796e2748bc3b877ca
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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