Dimethylformamide → HCID 22219969, compound

Participants

Reaction Conditions

Reaction Steps

6-chloronicotinic acid (1.0 g, 6.3 mmol)) was added portion-wise over 30 min to a stirred suspension of sodium hydride (60%, 0.76 g, 19 mmol) in toluene (10 mL. The mixture was stirred for 30 min then cooled to 0° C. A solution of 3-chloro-benzyl alcohol (0.69 g, 6.4 mmol) in toluene (5 mL) was added drop-wise over 10 min. The mixture was warmed to room temperature, DMF (20 mL) was added and the mixture was heated to 95° C. and stirred for 18 h. The mixture was cooled to room temperature then poured into water (30 mL). The aqueous mixture was acidified to pH 2 and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water and brine, then dried over sodium sulfate and concentrated in vacuo to give a yellow solid (2.36 g). The residue was re-crystallised [2-propanol-water, (2:1)] to give the product as a white solid (0.85 g, 51%), m.p. 158° C. (dec.). 1H-NMR (400 MHz, CDCl3): 8.93 (1H, d, J=2.5 Hz), 8.24 (1H, dd, J=2.5, 8.5 Hz), 7.46 (1H, s), 7.35–7.29 (3H, m), 6.87 (1H, dd, J=1, 8.5 Hz) and 5.45 (2H, s).

Provenance & Evidence