Isatin → HCID 3661139, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of isatin (7.35 g) in N,N-dimethylformamide (70 ml) was added potassium tert-butoxide (6.98 g) under cooling at 5° C., and the reaction mixture was stirred for 10 minutes at the same temperature. To the mixture was added dropwise a solution of 1,4-dibromobutane (54 g) in N,N-dimethylformamide (25 ml), and stirred for an hour at 18° C. The reaction mixture was poured into ice-water, and extracted with chloroform. The extracts were combined, washed with water and evaporated. After addition of n-hexane (200 ml) to the residue, the solvent was decanted and then to the residue was added chloroform (20 ml). The mixture was filtered to remove insoluble substances and the filtrate was subjected to column chromatography on silica gel (50 g), eluted with chloroform. The fractions containing the object compound were collected, and concentrated to give dark red oil of 1-(4-bromobutyl)isatin (7.52 g).

Provenance & Evidence