Acetic Acid → 4-Chloro-N,N-dimethylpyridin-2-amine

Participants

Reaction Steps

Acetic acid (0.6 ml, 10.5 mmol) was added dropwise to a solution of 2-amino-4-chloropyridine (384 mg, 3.0 mmol), formaldehyde (2.4 ml of a 37% aqueous solution, 29.6 mmol) and NaBH3CN (581 mg, 9.0 mmol) in MeCN (10 ml) and water (2 ml) at 0° C. After 10 minutes the reaction was warmed to room temperature and stirred for 3 days. The reaction was basified to pH4 with 1M aq. NaOH and then extracted with diethyl ether (3×30 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (Hexane/Diethyl ether with gradient, 98:2 to 8:2) to provide the title compound as colourless oil (260 mg, 56%).

Provenance & Evidence