Cyclooctylamine → HCID 20375715, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclooctylamine (12.7 g., 0.10 mole) in chloroform (50 ml.) at 10°-20° C. is added dropwise ethyloxalyl chloride (6.83 g., 0.05 mole) in chloroform (50 ml.) over a period of 30 minutes. After stirring for 2 additional hours at 10° C., the mixture is washed with H2O (4×50 ml.), and the organic layer dried over Na2SO4. After filtration and evaporation an oil is obtained (11.3 g.). To the crude ethyl N-cyclooctyloxamate dissolved in ethanol (27 ml.) is added sodium (1.15 g., 0.05 mole) dissolved in absolute ethanol (35 ml.) and the mixture is stirred overnight. Following evaporation, the residue is dissolved in H2O (41 ml.) with heating, and the solution filtered while hot. The filtrate is acidified with 6 N HCl, and the resulting slurry cooled at ice temperature. The solid obtained by filtration is recrystallized from boiling H2O (100 ml.) to give N-cyclooctyloxamic acid, m.p. 115°-116° C.

Provenance & Evidence