Triethylamine → 6-(2-Tert-butoxy-2-oxoethoxy)quinoline-3-carboxylic acid

Participants

Reaction Steps

Methanol (100 mL) and triethylamine (4.5 mL, 33 mmol) were added to 6-(2-tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acid (1.27 g, 3.76 mmol). 10% Palladium on carbon (350 mg) was added and the reaction was pressurized to 17 psi hydrogen. The reaction was agitated at room temperature for 3 hours. The reaction mixture was diluted with methanol and filtered through Celite. The filtrate was concentrated to a yellow solid. The solid was diluted with water and the mixture was acidified to pH=4 with 1 N aqueous hydrochloric acid. The solid was collected by filtration, washed with water, and dried under vacuum to give the title compound (960 mg, 84%) as a pale yellow solid. +ESI (M+H) 304.2; 1H NMR (400 MHz, CD3OD, δ): 9.19 (d, J=2.15 Hz, 1 H), 8.87 (d, J=2.15 Hz, 1 H), 8.01 (d, J=9.36 Hz, 1 H), 7.59 (dd, J=9.27, 2.83 Hz, 1 H), 7.38 (d, J=2.73 Hz, 1 H), 4.78 (s, 2 H), 1.49 (s, 9 H).

Provenance & Evidence