Hydrochloric Acid → HCID 21220537, compound

Participants

Reaction Steps

2-(3-Chlorophenyl)-4,4a,5,6-tetrahydropyrido[3,4-h]cinnolin-3(2H)-one (from Example 5 above; 66 mg) was placed in a flask under nitrogen. Borane tetrahydrofuran complex (1.0M in THF; 3 ml) was added and the solution stirred for 16 hours at ambient temperature. The mixture was added to methanol (3 ml) with stirring and then concentrated hydrochloric acid (0.5 ml) was added cautiously. The mixture was heated under reflux for 30 minutes, then cooled to room temperature and the volatiles removed on a rotary evaporator. The resultant product was partitioned between NaHCO3 (aqueous) and ethyl acetate. The aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated to give a solid which was chromatographed eluting with ethyl acetate to give a solid which was recrystallised from isopropanol to yield the title compound as yellow crystals (14 mg).

Provenance & Evidence