3,4-Dichloro-N-(5-chloro-2-hydroxy-4-nitrophenyl)benzamide → N-(4-Amino-5-chloro-2-hydroxyphenyl)-3,4-dichlorobenzamide

HRID 47180Notes

Reaction equation

HRID 47180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([N+:15]([O-])=O)=[CH:10][C:9]=1[OH:18])=[O:6]>C(OCC)(=O)C.CN(C)C=O.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([NH2:15])=[CH:10][C:9]=1[OH:18])=[O:6]

Participants

5

Reactant 1

HCID 120977653,4-Dichloro-N-(5-chloro-2-hydroxy-4-nitrophenyl)benzamide

Product 1

HCID 15508679N-(4-Amino-5-chloro-2-hydroxyphenyl)-3,4-dichlorobenzamideYield 84%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The nitrophenol (3) (36.0 g, 0.1 mol) was dissolved in ethyl acetate (250 ml) and dimethylformamide (DMF) (50 ml). The solution was hydrogenated over Raney Nickel at 3040 kPa (30 atm)/25 C. for 15 h. The catalyst was removed by filtration through a pad of Kieselguhr and the ethyl acetate removed in vacuo. The residual solution of aminophenol (4) in DMF was poured on to an ice/water mixture (1.51) to precipitate aminophenol (4) (27 g, yield 84%), which was collected by filtration and dried. This was stored under a blanket of nitrogen while the ballast acid chloride was prepared.

Workup

  1. customThe catalyst was removed by filtration through a pad of Kieselguhr
  2. customthe ethyl acetate removed in vacuo
  3. additionThe residual solution of aminophenol (4) in DMF was poured on to an ice/water mixture (1.51)

Sources & evidence

ORD record
ord-d27fadb077d34d4e97ac9a4ceb72c1bc
Source dataset
uspto-grants-2004_03
Patent number
US06699650B1

Reaction notes

Loading…