Cyanogen Bromide → HCID 20323749, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.6 g (0.0129 mole) of 5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1] benzopyrano[3,4-d]pyridine, 1.38 g (0.013 mole) of cyanogen bromide, 2.13 g (0.026 mole) of sodium acetate and 35 ml of methanol was stirred at 0° C for 3 hours, and then at ambient temperature for 12 hours. After removal of the solvent under reduced pressure, water was added to the residue and the mixture was extracted with diethyl ether. The organic layer was washed with 2 N HCl, followed by saturated NaCl solution. The ether layer was separated, dried over Na2SO4 and concentrated to give 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine as a yellow oil (4.9 g, 99% yield) which crystallized upon standing.

Provenance & Evidence