Hydrochloric Acid → 2-Chloro-4-methyl-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

Copper(II)chloride (10.01 g, 74.5 mmol) was dissolved in N,N-dimethylformamide (75 mL) and the solution was warmed to 60° C. A solution of 2-amino-4-methyl-5-nitropyridine (9.50 g, 62.0 mmol) in N,N-dimethylformamide (145 mL) was added with addition funnel over 0.5 h. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was cooled to room temperature and poured into 3 N aqueous hydrochloric acid (300 mL), followed by extraction with diethyl ether. The organic extract was dried over sodium sulfate and adsorbed onto silica gel for purification by column chromatography (SiO2, 20:3 hexanes/ethyl acetate). 2-Chloro-4-methyl-5-nitropyridine was obtained as a yellow solid (2.10 g, 20%): 1H NMR (300 MHz, CD3OD) δ2.63 (3H, s), 7.60 (1H, s), 8.96 (1H, s); ESI MS m/z 173 [C6H5ClN2O2+H]+.

Provenance & Evidence