Triethylamine → HCID 70369569, compound

Participants

Reaction Steps

To a mixture of quinolin-2-amine (200 mg, 1.4 mmol) and triethylamine (210 mg, 2.1 mmol) in dichloromethane (10 mL) was added dropwise ethyl 2-chloro-2-oxoacetate (227 mg, 1.67 mmol). After stirring for 1 hour at room temperature, the reaction was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1% ethyl acetate in petroleum ether to afford ethyl 2-oxo-2-(quinolin-2-ylamino)acetate as yellow solid (210 mg, 62%). (ES, m/z): [M+H]+ 245.1; 1H NMR (400 MHz, CDCl3): δ 9.65 (br s, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.24 (d, J=8.8 Hz, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.74-7.69 (m, 1H), 7.53-7.49 (m, 1H), 4.46 (q, J=7.2 Hz, 2H), 1.46 (t, J=7.2 Hz, 3H).

Provenance & Evidence