Triethylamine → HCID 66856518, compound

Participants

Reaction Steps

To a solution containing 6-bromo-2-oxo-3-(thiophene-2-yl)-1,2-dihydroquinoline-4-carboxylic acid (1.00 g, 2.86 mmol) in tetrahydrofuran (11.4 ml) were added isobutyl chloroformate (0.364 ml, 2.86 mmol) and triethylamine (0.398 ml, 2.86 mmol) at 0° C. The reaction was allowed to stir at room temperature for 30 min. The reaction was then filtered to remove solids and placed in an ice bath at 0° C. Sodium borohydride (0.119 g, 3.14 mmol) was added to the reaction mixture followed by methanol (3 ml). This mixture was allowed to warm to room temperature and stirred for 4 h. The reaction was diluted in ethyl acetate (50 ml) and extracted with 1 N sodium hydroxide (3×40 ml) and sodium chloride (1×40 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated to afford 6-bromo-4-(hydroxymethyl)-3-(thiophen-2-yl)quinolin-2(1H)-one as a crude, yellow oil. Compound used without further purification. LCMS (M+H)=337.7.

Provenance & Evidence