1-Hydroxybenzotriazole → Butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate

Participants

Reaction Steps

To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3-carboxylic acid (0.1 g) in dichloromethane EDC.HCl (1-Ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride, 0.161 g), HOBt (N-hydroxybenzotriazole 0.042 g), DMAP (4-dimethylaminopyridine, 0.17 g) and n-butanol (25 mL) were added, and the reaction mixture was stirred at room temperature for 3 hours. After aqueous work up, the reaction mixture was extracted, concentrated and dried over anhydrous sodium sulphate to afford the crude product which was later purified by column chromatography to afford 0.05 g (55% yield) of butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 10.84 (s, 1H, —NH—), 9.21 (s, 1H, aromatic), 8.05 (d, 1H, J=8.8 Hz, aromatic), 7.97 (d, 1H, J=8.8 Hz, aromatic), 7.80 (s, 1H, aromatic), 7.16 (d, 2H, J=8.7 Hz, aromatic), 6.96 (d, 2H, J=8.7 Hz, aromatic), 5.60 (s, 1H, —NHCH3—), 4.41 (t, 2H, J=6.6 Hz, —O—CH2—), 3.87 (s, 3H, —OCH3), 2.88 (s, 3H, —NCH3), 1.92-1.75 (m, 2H, —O—CH2—CH2—CH2—), 1.65-1.46 (m, 2H, —O—CH2—CH2—CH2—), 1.12-0.98 (m, 3H, —CH3); LC-MS (m/z) 407.9 (M+1).

Provenance & Evidence