3,4-Dichlorobenzoic acid → HCID 12940206, compound

Participants

Reaction Steps

A mixture of 3,4-dichlorobenzoic acid (6.5 g) and 25 ml of SOCl2 were refluxed for 3 hours and concentrated in vacuo. The concentrate was dissolved in 10 ml of toluene and added dropwise to a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (8 g, 0.03 mole) in 200 ml of toluene and 75 ml of 20% NaOH. The mixture was stirred in the cold for 1 hour whereupon the solid material was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol-chloroform (7:2:1) as eluant. This major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and methanol, isolated by evaporation of the solvent and recrystallized from methanol-ethyl acetate to yield 3.8 g of the desired product, m.p. (decomposed at 271°-3°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR22##

Provenance & Evidence