Reaction #45832

Reaction equation

4-amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methyl-5-nitrobiphenyl-3-carbonitrile

→

compound

Yield 97.3%

4,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile

Yield 97.3%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   OtherThe insoluble matter was removed by filtration under suction
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate
3. 3
   Washwashed with aqueous saturated sodium carbonate solution and saturated brine in that order
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherThe solvent was evaporated away under reduced pressure
6. 6
   Otherby drying with a vacuum pump

Procedure

An aqueous solution (14 ml) of iron chloride hexahydrate (0.83 g, 3.06 mmol) and zinc (5.01 g, 76.6 mmol) were added to an N,N-dimethylformamide (35 ml) solution of 4-amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methyl-5-nitrobiphenyl-3-carbonitrile (I-268) (1.40 g, 3.83 mmol), followed by stirring at room temperature for 1 hour. The insoluble matter was removed by filtration under suction, then the filtrate was diluted with ethyl acetate, washed with aqueous saturated sodium carbonate solution and saturated brine in that order, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, followed by drying with a vacuum pump to obtain the entitled compound (1.25 g, 97%) as a dark brown solid.

Source