Ethyl chloroformate → Methyl(1,3,4,9-tetrahydro-2H-carbazol-2-yl)carbamic acid, ethyl ester

Participants

Reaction Steps

A solution of 0.05 mol of 2,3,4,9-tetrahydro-N-methyl-1H-carbazol-2-amine in 450 ml of CH2Cl2 and 185 ml of saturated aqueous NaHCO3 was stirred vigorously at room temperature and treated dropwise during 30 min with a solution of 0.15 mol of ethyl chloroformate in an equal volume of CH2Cl2. After stirring vigorously for 5 hr, the CH2Cl2 layer was separated, washed in succession with 10% aqueous K2CO3, H2O, 0.1 N hydrochloric acid, H2O, and dried over anhydrous Na2SO4. The residue remaining after evaporation of the CH2Cl2 was recrystallized from ethanol to give the title compound, mp 167°-168°.

Provenance & Evidence