Sodium Carbonate → 2'-Amino-2-methoxy-1'-methyl-7-bromo-10,11-dihydrospiro[dibenzo[a,d][7]-annulene-5,4'-imidazol]-5'(1'H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-2-methoxy-1-methyl-11,12-dihydro-dibenzo[a,e]cyclo-octene-5,6-dione 13 (2.49 g; 6.9 mmol) in dioxane and ethanol was treated with N-methylguanidine (1.52 g, 13.9 mmol), followed by a solution of sodium carbonate (1.47 g; 13.9 mmol) in water, heated at 85° C. for 3 hours, cooled and concentrated in vacuo. The resultant residue was taken up in chloroform and washed with water. The chloroform phase was separated, dried over magnesium sulfate and evaporated. This residue was crystallized from ethyl acetate and hexane to give the title product as a tan powder, 1.62 g (57% yield, identified by NMR and mass spectral analyses.

Provenance & Evidence