Dimethylacetamide → Corypalline

Participants

Reaction Steps

2,3',4'-Trimethoxy-5-methyl-4-nitrodiphenyl ether (2e) (6.38 g) was added to N,N-dimethyl acetamide (125 ml) under nitrogen, stirred for 5 min., and treated with 2 -methyl-6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium iodide (1) (7.65 g). Potassium t-butoxide (4.39 g) was then added in small portions over 15 min. The reaction mixture was stirred under nitrogen at room temperature for 7 hours, diluted with cold water (600 ml), stirred for 10-15 min. and refrigerated overnight. The supernatant aqueous layer was decanted from the solid which was collected and washed with 1:1 methanol-ether (20 ml) followed by ether (100 ml) and sucked dry (9.40 g, 92%), to yield 1-[2'-nitro-4'-methoxy-5'-(3", 4"-dimethoxy)phenoxybenzyl]-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (3e), mp 169°-171°. An analytical sample was crystallized from chloroform-methanol: mp 173°-174°; nmr δ 2.40 (3H, NCH3), 3.85, 3.88, 3.92, and 3.98 (each 3H, 4 OCH3), 6.37-7.60 (7H, ArH).

Provenance & Evidence