Indoline → HCID 13324709, compound

Participants

Reaction Steps

4.94 g (0.206 mole) 99% NaH was added in one portion to a solution of 21.6 ml (0.188 mole) indoline in 85 ml sieve dried dimethylsulfoxide (DMSO) at room temperature. The resulting slurry was permitted to stir at room temperature for 2 hours and then cooled in an ice bath. A solution of 25 g (0.206 moles) 2-fluorobenzonitrile in 35 ml DMSO was added dropwise. At the end of the addition, the ice bath was removed and the mixture was permitted to stir at room temperature overnight (about 16 hours). The product was poured onto 300 ml of ice and extracted with CHCl3 (300 ml). The organic phase was thrice washed with water (500 ml portions), brine (500 ml), dried (Na2SO4) and concentrated to give 39.9 g (96.4%) of crude material. Two recrystallizations from isopropyl ether afforded 4-(1-indolinyl)benzonitrile, m.p. 88.5°-89.5° C.

Provenance & Evidence