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

Temperature

60 °C

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]+.

1. temperatureThe reaction mixture was heated at 110° C. for 16 h
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionfollowed by extraction with diethyl ether
4. extractionThe organic extract
5. dry with materialwas dried over sodium sulfate
6. customadsorbed onto silica gel for purification by column chromatography (SiO2, 20:3 hexanes/ethyl acetate)

ORD record

ord-d19c4b37b8ce46808f097ef63b37bec3

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608627B2