Reaction #75458

Reaction equation

nitrophenol

2-(3,4-dichlorobenzamido)-4-chloro-5-nitrophenol

→

aminophenol

Yield 84.0%

2-(3,4-Dichlorobenzamido)-4-chloro-5-aminophenol

Yield 84.0%

Solvents

ethyl acetate

dimethylformamide

Conditions

Workup

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

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.

Source