Sodium Hydroxide → HCID 86735704, compound

Participants

Reaction Steps

To a suspension of 6.6 g (0.02 mole) of 5-formyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole (Example 69) and 2.0 g (0.03 mole) of hydroxylamine hydrochloride in 25 ml of ethanol was added dropwise a solution of 1.6 g (.04 mole) of sodium hydroxide in 5 ml of water. The reaction mixture was stirred for 30 minutes and heated under reflux for 5 minutes. A yellow solid precipitated. The reaction mixture was diluted with water, extracted with methylene chloride, and the extract was dried over potassium carbonate and concentrated. The resulting oil was dissolved in ether and filtered. Evaporation of the ether gave the product, 5-formyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole oxime, as an oil which was crystallized by the addition of pet. ether. The oxime was dissolved in ether and the solution was acidified to give 3.8 g of the hydrochloride salt; mp. 200° -205° (with dec. starting at 185°).

Provenance & Evidence