2-Methoxybenzoyl chloride → HCID 12940216, compound

Participants

Reaction Steps

To a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine, (7 g, 0.026 mole) in 200 ml of toluene and 75 ml of 20% NaOH, was added dropwise 4.8 g of 2-anisoyl chloride in toluene. The mixture was stirred in the cold for 1 hour after which the toluene layer was collected, dried over MgSO4 and concentrated in vacuo. The concentrate was chromatographed over silica gel using ethyl acetate-methanol (4:1) as eluant. The major fraction (6.5 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and the mixture concentrated by removal of the solvent in vacuo. The salt was crystallized from acetone and twice recrystallized from methanol-ethyl acetate to yield 3.0 g of the desired product, m.p. (decomposed at 243°-4°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR27##

Provenance & Evidence