Sodium Hydroxide → HCID 19810693, compound

Participants

Reaction Steps

A solution of 3-dimethylaminoacrylaldehyde (3.68 g) in dry acetonitrile (10 ml) was slowly added over a 30-minute period to a solution of phosphorus oxychloride (6.07 g) in dry acetonitrile (10 ml) with stirring at 0°-10° C. under nitrogen. A solution of 5,6-dihydro-4,4-dimethyl-1-(4-fluorophenyl)-4H-pyrrolo[3,2,1-ij]quinoline (3.70 g) in dry acetonitrile (9 ml) was slowly added to the reaction mixture at the same temperature. The reaction mixture was refluxed for 7 l hours under nitrogen, cooled to room temperature and slowly poured into a cold solution of sodium hydroxide (6.34 g) in water (130 ml) with stirring. The reaction mixture was extracted twice with toluene. The extracts were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of n-hexane and ethyl acetate (5:1, V/V). The fractions containing the object compound were collected and evaporated under reduced pressure. The residual oil was triturated with n-hexane to give yellow crystals of (E)-3-[5,6-dihydro-4,4-dimethyl-1-(4-fluorophenyl)-4H-pyrrolo[3,2,1-ij]quinolin-2-yl]acrylaldehyde (3.11 g).

Provenance & Evidence