Hydrochloric Acid → 5,6,7,8-Tetrahydroquinoline-8-carbothioamide

Participants

Reaction Steps

A 5,6,7,8-tetrahydroquinoline (0.01 mole) in the solvent indicated (approx. 15 ml) at 0° C. under nitrogen was treated with an alkyl lithium or a lithium amide (0.01 mole). To this solution of the 5,6,7,8-tetrahydro-8-lithioquinoline was added, at around 0° C. under nitrogen, the silyl isothiocyanate (0.01 mole) and the mixture was stirred 15 minutes. H2O(10 ml) and 2N HCl (15 ml) were added and the acid layer was separated and washed with ethyl acetate. The aqueous solution was basified (Na2CO3) and extracted with chloroform. The chloroform extracts were dried (MgSO4) and evaporated to give the 5,6,7,8-tetrahydroquinoline-8-thiocarboxamide. In this manner the thioamides in the table were prepared.

Provenance & Evidence