Methanol → HCID 86588219, compound

Participants

Reaction Steps

A mixture of 2.17 g (9.37 mmol) 1-(2-chloro-quinolin-5-yl)-2-diazo-ethanone and 20 mL methanol was brought to reflux. A solution of 0.20 g (0.87 mmol) silver benzoate in 1 mL triethylamine was added to the reaction mixture. After 10 min at reflux, TLC analysis (ethyl acetate, silica, Rf prod 0.8) showed starting material consumed. The solvent was removed under reduced pressure and the resulting black residue was purified on 100 g 230-400 mesh silica eluting with 1:1 hexanes/ethyl acetate to give 1.20 g (5.09 mmol, 55%) of (2-chloro-quinolin-5-yl)-acetic acid methyl ester as a white amorphous solid. MS (APCI) m/z 236 (M, 100% abundance), 238 (M+2, 32% abundance). 1H NMR (400 MHz) CDCl3 8.31 (d, J=8.9 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.74 (m, 1H), 7.49 (d, J=7.2 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 4.05 (s, 2H), 3.68 (s, 3H).

Provenance & Evidence