HCID 90273223, compound → HCID 90273273, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-2,6-dimethyl-5-nitropyridin-4(1H)-one (0.59 g, 2.006 mmol) and copper(I) cyanide (0.359 g, 4.01 mmol) in N-methyl-2-pyrrolidone (NMP) (10 mL) was heated at 125° C. for 2 h, at which time it was allowed to cool to ambient temperature and poured into ice/water/saturated NH4Cl (100 mL). The mixture was stirred for 15 min (pH˜6-7), then allowed to stand in an ice bath for 1 h. The solids were filtered, washed with a small amount of water, air dried for 10 min, and further dried in a vacuum oven at 37° C. for 18 h to give 2,6-dimethyl-5-nitro-4-oxo-1,4-dihydropyridine-3-carbonitrile (176 mg, 0.820 mmol, 40.9% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.30-2.38 (m, 3 H) 2.44-2.48 (m, 3 H) 12.78 (br. s., 1 H). MS(ES) [M+H]+ 193.9.

Provenance & Evidence