Ethanol → 2-(3-Amino-4-chlorobenzoyl)-benzo[b]furan

HRID 263291Notes

Reaction equation

HRID 263291 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:19]([O-])=O.C(O)C>C(O)(=O)C.[Ni].[Al]>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[Cl:1])[C:6]([C:8]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 213166292-(4-Chloro-3-nitrobenzoyl)-benzo[b]furan

Product 1

HCID 213166422-(3-Amino-4-chlorobenzoyl)-benzo[b]furan

Reagents, catalysts & solvents 2

HCID 6336846Nickel aluminideCatalystHCID 176Acetic AcidSolvent

Procedure

37 g 2-(4-Chloro-3-nitrobenzoyl)-benzo[b]furan are refluxed with agitation for 4 hours in a mixture of 500 ml 50% aqueous acetic acid, 250 ml ethanol and 90 g powdered nickel/aluminum alloy (1:1). After filtration of the metal powder, the solvent is distilled off, water is added to the residue, and extraction is carried out with ethyl acetate. After evaporation of the solvent, colorless crystals having a melting point of 137° C. (from isopropanol) are obtained.

Workup

  1. filtrationAfter filtration of the metal powder
  2. distillationthe solvent is distilled off
  3. additionwater is added to the residue, and extraction
  4. customAfter evaporation of the solvent, colorless crystals
  5. customare obtained

Sources & evidence

ORD record
ord-bf5e69f009464d7c963cb4c7df0b393f
Source dataset
uspto-grants-1979_05
Patent number
US04156732

Reaction notes

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