Hydrogen Bromide → HCID 86745037, compound

Participants

Reaction Steps

(See FIG. 2) A suspension of 0.456 g. (1.44 mmol) of 11-methoxy-6- methyl-hexahydrobenzo[a]phenanthridine hydrochloride in 10 ml 48% HBr was heated for 2.5 hours at reflux under N2 in an oil bath. The heat was removed, and the reaction mixture was placed in the refrigerator overnight. The white precipitate was collected by suction filtration, and after washing the crystals on the filter with cold ethanol and ether, the product weighed 403 mg (80.6%), mp 251°-254° C. The filtrate was concentrated and the residue was crystallized from ethanol to provide additional product, giving essentially a quantitative total yield of the phenol, mp 254° C. CIMS (NH3): M+1 266; 1H-NMR (CDCl3, free base); δ 7.38 (d, 1, ArH, J=7.5 Hz), 7.22 (m, 3, ArH), 7.04 (d, 1, ArH, J=8.2 Hz), 6.69 (s, 1, ArH); 6.64 (d, 1, ArH, J=8.2 Hz,) 3.98 (d, 1, Ar2CH), 3.84 (d, 1, ArCH2N, J=14.5 Hz), 3.50 (d, 1, ArCH2N, J=14.5 Hz), 2.87 (m, 2, CH2 and CHN) 2.38 (s, 3, NCH3), 2.09 (m, 2, CH), 1.86 (m, 1, CH2CN).

Provenance & Evidence