Potassium Hydroxide → 10-Amino-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]pyridine

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Reaction Conditions

Reaction Steps

A solution of 7.07 g. (0.02 mole) of 10-hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]-pyridine in 100 ml. of dimethylformamide was added to a stirred suspension of 1.06 g. (0.022 mole) of 50% sodium hydride (dispersed in mineral oil), in 20 ml. of dimethylformamide. The mixture was stirred at 80° C. for 1-1/2 hour and after cooling to room temperature, 4.8 g. (0.02 mole) of 4-chloro-2-phenylquinazoline was added. The mixture was stirred at 100° C. for 15 hours, and then at 150° C. for 4 hours. The cooled mixture was poured into water and extracted with ether. The combined ether extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by chromatography on a Florisil (60-100 mesh) column using chloroform to give 7.5 g. of the O-alkylated product. The O-alkylated product was heated in a Woods' metal bath at 330° C. under nitrogen for 3 hours. The crude product was purified by chromatography on a Florisil column using graded chloroform-methanol mixtures to give 6.6 g. of the rearranged product. A mixture of 6.6 g. of the rearranged product and 60 g. of potassium hydroxide in 40 ml. of water and 800 ml. of ethylene glycol was stirred and heated at 150° C. for 18 hours. The mixture was diluted with water and extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a Florisil column using chloroform to yield the pure product.

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