Sodium Chloride → HCID 10486994, compound

Participants

Reaction Steps

1-(3-Iodopropyl)pyrrol-2-acetonitrile (31 g., 0.128 moles) is dissolved in dry dimethylformanide (35 ml.) is added with stirring to a cooled (-5°) suspension of sodium hydride (50%, 7.5 g., 0.156 moles) in dry dimethylformamide (100 ml.), maintained in an atmosphere of dry nitrogen, at a rate such that the reaction temperature is maintained between -5° to +5°. When the addition is completed, stirring at this temperature is continued for 1 hour at which time the starting material is shown to be absent by t.l.c. (silica gel, hexane-ethyl acetate, 1:1). A cold, dilute solution of sodium chloride (150 ml.) is added to the reaction during 15 minutes and the product is extracted into benzene. The extract is washed with dilute sodium chloride solution (3 times), with water (once) and then it is dried over sodium sulfate. The solvent is removed in vacuo leaving an oil (21.1 g.) which is chromatographed on silica gel. The crystalline product (13.6 g., 72%) is eluted with hexane-ethyl acetate (97.5:25 and 95:5). Crystallization from hexane-acetone yields 8-cyano-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine (XIX, n is 1), m.p. 47°-49°.

Provenance & Evidence