4-Nitrobenzoyl chloride → HCID 12940196, compound

Participants

Reaction Steps

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9, 10-dimethoxy-2H-benzo[a]quinolizine (7 g), 200 ml of toluene and 50 ml of 20% NaOH was cooled to below 10° and a solution of 4-nitrobenzoyl chloride (5 g) in toluene was added dropwise with stirring. The mixture was stirred in the cold for 1 hour and allowed to come to room temperature whereupon the solid was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol (6:1) as eluant. The major fraction (5.3 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and the solvent was removed in vacuo. The salt was crystallized from methanol-ether to yield 1.5 g of the desired product, m.p. (decomposed at 269°-70°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR17##

Provenance & Evidence