3,3-Dibromo-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile → 2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile
Reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][C:3]1=[O:13]>C(O)(=O)C.[Zn]>[O:13]=[C:3]1[CH2:2][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3,3-Dibromo-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile (10.5 grams, 33.3 mmole) and Zn dust (22.0 grams, 338.5 mmole) in acetic acid (250 ml) was stirred at room temperature for 45 minutes. The mixture was filtered through celite and concentrated to dryness. The resulting oil was diluted with 300 ml water and extracted with ethyl acetate. The combined extracts were washed with 1 N sodium hydroxide and brine, dried over MgSO4, filtered, and concentrated to give a white solid (1.9 g). MW 158.