(7-Chloro-2-methyl-quinolin-8-yl)-acetic acid tert-butyl ester → (7-Chloro-2-methyl-quinolin-8-yl)-acetic acid ethyl ester

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Reaction Conditions

Reaction Steps

(7-Chloro-2-methyl-quinolin-8-yl)-acetic acid tert-butyl ester (650 mg, 2.23 mmol) was dissolved in ethanol (13 ml) saturated with HCl gas. The solution was heated to 90° C. for 10 minutes. After cooling, volatiles were removed in vacuo, and the residue was purified via flash chromatography (gradient of hexane: EtOAc 95:5 to 80:20) to afford the title compound (372 mg, 63%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=8.00 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.48 (d, J=9.2 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H); 4.52 (s, 2H), 4.19 (q, J=7.3 Hz, 2H), 2.81 (s, 3H), 1.27 (t, J=7.3 Hz, 3H). MS (ES+): 264.2 (M+H)+.

Provenance & Evidence