Sodium Cyanide → HCID 13324753, compound

Participants

Reaction Steps

A mixture of 10.2 g (ca. 33.8 mmole) of 3-(1-indolinyl)benzenemethanesulfonic acid methyl ester of Example 20c and 4.97 g (101.4 mmole, 3.0 equiv.) sodium cyanide in 200 ml sieve dried DMF was heated at 60°-70° C. for 50 minutes. The product was concentrated under high vacuum at 50°-60° C. and the residue was partitioned between chloroform (200 ml) and water (200 ml). The organic portion was washed twice with 200 ml water, 200 ml brine, dried over Na2SO4 and concentrated under vacuum to give 6.39 g (80.7%) of product. Kugelrohr distillation of a 0.8 g sample gave 0.6 g of an oil of 3-(1-indolinyl)benzeneacetonitrile, b.p. 189°-192° C./0.15 mm.

Provenance & Evidence