Ethyl chloroformate → (S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonyloxy)-2-phenylquinoline-4-carboxamide

Participants

Reaction Steps

0.5 g (1.3 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved in 10 ml of pyridine; 0.5 ml (5.2 mmol) of ethyl chloroformate were added dropwise and the solution was refluxed under magnetical stirring for 8 hours. The reaction mixture was allowed to reach room temperature and left overnight. 1.0 ml (10.4 mmol) of ethyl chloroformate were added and the solution refluxed for 4 hours. The pyridine was evaporated off with toluene; the residue was dissolved in CH2Cl2, washed with H2O and the organic layer dried over na2SO4 and evaporated in-vacuo to dryness. The crude product was triturated with warm i-Pr2O to yield 0.25 g of the title compound as a yellow solid.

Provenance & Evidence