Potassium Carbonate → (S)-N-(alpha-ethylbenzyl)-3-(aminocarbonylmethoxy)-2-phenyquinoline-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, under nitrogen atmosphere and magnetic stirring, in 5 ml of THF; 0.5 g (3.6 mmol) of K2CO3, 0.27 g (1.9 mmol) of 2-bromoacetamide and a small amount of KI were added. The reaction mixture was left overnight under magnetical stirring; the precipitate was filtered off and the residue dissolved in H2O and extracted with EtOAc; the organic layer was washed with sat. sol. NaCl, dried over Na2SO4 and evaporated in-vacuo to dryness. The crude product was triturated with hexane and then recrystallized form EtOH to yield 0.29 g of the title compound as a white solid.

Provenance & Evidence