2-Chloronicotinic acid → (2-Chloropyridin-3-yl)methanol

Participants

Reaction Steps

To a stirred solution of 2-chloronicotinic acid (10.0 g, 63.4 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added lithium aluminum hydride (63 mL of a 1.0M solution in THF, 63 mmol) over 10 minutes. The solution was allowed to warm to room temperature over 2 h. Small quantities of ice were carefully added to quench the reaction followed by water. The aqueous solution was extracted with ether. The combined organic extracts were washed with water and saturated aqueous NaCl, dried over MgSO4, and concentrated in vacuo to give the title compound of Step A as an orange solid (6.18 g). 1H NMR (CDCl3, 300 MHz) δ8.30 (dd, 1H), 7.90 (dd, 1H), 7.29 (dd, 1H), 4.80 (s,2H), 2.42 (br s,1H).

Provenance & Evidence