Methanol → Sodium 7-(4-fluorophenyl)quinoline-3-sulfinate

Participants

Reaction Steps

Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoate (4.23 g, 11.3 mmol) was dissolved/suspended in hot tetrahydrofuran (240 mL). Methanol (60 mL) was added and the mixture allowed to cool to about 30° C., at which point sodium methoxide (0.91 g, 17 mmol) was added and the resulting mixture stirred for 1 hour. The solid present was collected under suction, washed with tetrahydrofuran and dried in vacuo to afford a first crop of sodium 7-(4-fluorophenyl)quinoline-3-sulfinate (2.1 g). The filtrate was concentrated and the residue triturated with tetrahydrofuran. The solid was collected under suction, washed successively with small volumes of tetrahydrofuran, ice-cold water then tetrahydrofuran, and dried in vacuo to give a second crop of product (0.87 g). The combined yield of the title product was 2.97 g (85%). 1H NMR (500 MHz, CD3OD) δ 9.13 (1H, d, J 1.9 Hz), 8.52 (1H, d, J 1.6 Hz), 8.24 (1H, s), 8.11 (1H, d, J 8.5 Hz), 7.94 (1H, dd, J 1.7, 8.5 Hz), 7.84-7.82 (2H, m), 7.26 (2H, t, J 8.7 Hz).

Provenance & Evidence