Sodium Hydroxide → 7-Chlorofuro[2,3-c]pyridine

Participants

Reaction Steps

The mixture of furo[2,3-c]pyridin-7(6H)-one (12.0 g, 87.6 mmol) and phosphorous oxychloride (21.3 g, 139 mmol) was placed in an oven-dried two-necked flask, then was heated to reflux for 3-4 h under a nitrogen atmosphere. The reaction mixture was cooled to RT, then poured into ice-cold water (250 mL). After it was basified with 10% aq. NaOH solution, the mixture was extracted with diethyl ether (3×100 mL), dried over anhydrous potassium carbonate, filtered and concentrated to give 10.0 g (75%) of the title compound as brown crystals. 1H NMR (300 MHz, CDCl3): δ 6.87 (d, J=1.8 Hz, 1H), 7.50 (d, J=6.0 Hz, 1H), 7.82 (d, J=1.8 Hz, 1H), 8.20 (d, J=6.0 Hz, 1H).

Provenance & Evidence