Acetone → Methyl 3-amino-4-phenoxy-5-sulfamoylbenzoate

HRID 971882Notes

Reaction equation

HRID 971882 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([N+:21]([O-])=O)[CH:5]=1.CC(C)=O>CO.[Ni]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([NH2:21])[CH:5]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 53854447Methyl 3-nitro-4-phenoxy-5-sulfamoylbenzoate

Product 1

HCID 13020993Methyl 3-amino-4-phenoxy-5-sulfamoylbenzoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

35 g (~0.1 mol) of 3-nitro-4-phenoxy-5-sulphamylbenzoic acid methyl ester are suspended in 150 ml of methanol and are hydrogenated with Raney nickel (5-10%) in an autoclave at 40°-50° and 100 atmospheres gauge. The precipitated amino compound is dissolved by the addition of acetone on a steambath and the Raney nickel is removed by filtration.

Workup

  1. customthe Raney nickel is removed by filtration

Sources & evidence

ORD record
ord-df729b4a8bae4a13801431d1224c069c
Source dataset
uspto-grants-1979_07
Patent number
US04161531

Reaction notes

Loading…