Acetic Anhydride → HCID 18958952, compound

Participants

Reaction Steps

A mixture of 5-(3-aminopyrid-4-ylamino)-2-cyanoindane (12.28 g, ca 44.5 mmol from step (d) above), acetic acid (70 ml) and acetic anhydride (70 ml) was heated at reflux under nitrogen for 1.75 hours, cooled, and concentrated under reduced pressure. The residual brown gum was dissolved in 2M hydrochloric acid (40 ml) and washed with ethyl acetate (50 ml). The aqueous layer was rendered basic by the addition of 2M aqueous sodium hydroxide, and the product was extracted into dichloromethane. The combined extracts were wahsed with water (50 ml), dried over magnesium sulphate and the solvent evaporated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/methanol (7:1), to give a brown gum, which was recrystallised from ethyl acetate/methanol, to give the 2-cyano-5-(2-methylimidazo[4,5-c]pyrid-1-yl)indane as an off-white powder (9.67 g, 79%), m.p. 174°-176° C. Found: C,74.4; H,5.2; N,20.7. C17H14N4 requires C,74.4; H,5.1; N,20.4%.

Provenance & Evidence