HCID 54334932, compound → HCID 53829657, compound

HRID 971889Notes

Reaction equation

HRID 971889 reaction equation
[CH3:1][O:2][C:3](=[O:25])[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][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([N+:22]([O-])=O)[CH:5]=1.[H][H]>C(OCC)(=O)C.[Ni]>[CH3:1][O:2][C:3](=[O:25])[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][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([NH2:22])[CH:5]=1

Participants

5

Reactant 2

HCID 54334932HCID 54334932, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53829657HCID 53829657, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

45 g of 3-nitro-4-(4'-methylphenoxy)-5-sulphamoylbenzoic acid methyl ester are suspended in 150 ml of ethyl acetate and hydrogenated for 5 hours with Raney nickel at 50° C. and a hydrogen pressure of 100 atmospheres gauge. After cooling, the Raney nickel is separated and the solution is concentrated to dryness. The 3-amino-4-(4'-methylphenoxy)-4-sulphamoylbenzoic acid methyl ester is recrystallised from mthanol/H2O. Crystals melting at 183°-185° C.

Workup

  1. temperatureAfter cooling
  2. customthe Raney nickel is separated
  3. concentrationthe solution is concentrated to dryness
  4. customThe 3-amino-4-(4'-methylphenoxy)-4-sulphamoylbenzoic acid methyl ester is recrystallised from mthanol/H2O

Sources & evidence

ORD record
ord-b4cc2edd5cf54aa8b7d0aa636d5e8a1d
Source dataset
uspto-grants-1979_07
Patent number
US04161531

Reaction notes

Loading…