Sodium Chloride → HCID 20203546, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-one oxime (2.2 g, 9 mmol) in ethanol (50 mL) containing 10% sodium hydroxide (36 mL) was treated with Raney alloy (3.15 g) at 35° C. over 20 minutes. The reaction mixture was stirred at 45° C. for 18 hours, then poured into ice water (100 mL), saturated with sodium chloride. The product was extracted with ether (3×75 mL), dried, and evaporated. The residue was dissolved in toluene (30 mL), and extracted with 3% hydrochloric acid (50 mL). The aqueous layer was separated, and basified with 50% sodium hydroxide upon cooling. The product was extracted with chloroform, dried over MgSO4, filtered, and evaporated. The dark oily residue was chromatographed on silica gel (50 g). Elution with chloroform afforded 1.87 g (91%) of the desired amine as an amber oil.

Provenance & Evidence