Ammonium Hydroxide → (+/-)-trans-2-Chloro-6-propyl-5,5a,6,7,8,9,9a,10-octahydropyrido[2,3-g]quinoline hydrochloride

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (272 g, 165 mL, 175 mol) was added over 6 hours to a solution of (±)-trans2-oxo-6-propyl-1,2,5,5a,6,7,8,9,9a,10-decahydropyrido -[2,3-g]quinoline (5.75 g, 23.4 mMol) in dimethylformamide (250 mL) at 135° C. The reaction was stirred at 135° C. for 17 hours, poured over ice, and made basic with NH4OH and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product as a brown oil. Purification by flash chromatography (5% methanol in methylene chloride, 0.5% NH4OH) gave the desired product as a brown oil (5.6 g, 90% yield).

Provenance & Evidence