3-Bromo-7-chloro-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine → 8'-Chloro-spiro[cyclohexane-1,3'-[3H][1,4]oxazino[2,3-c]quinoline]

Participants

Reaction Steps

A solution of 16.4 g of 3-bromo-7-chloro-N-[1-hydroxycyclohexylmethyl]-4-quinolinamine in 176 ml of dimethylformamide was stirred at room temperature and to it was added 7.54 g of potassium tert-butoxide. The mixture was heated at 130°-140° C. for twenty hours. The reaction mixture was then cooled to room temperature, quenched with water, and extracted with an ether/ethyl acetate solution. Evaporation of solvents resulted in a crude oil which was purified by HPLC using 2:1 hexane/ethyl acetate as the eluent. A solid resulted which was recrystallized from isopropanol to yield 4 g of crystalline solid with a melting point of 216°-218° C.

Provenance & Evidence