2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Cyano-3,4-dimethyl-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

2-Cyano-3-methyl-5-nitropyridine (0.33 g, 2 mmol) was dissolved in 10 mL of THF and cooled in a dry ice/acetone bath under nitrogen. Methylmagnesium bromide (1.33 mL, 4 mmol) was added via syringe over five mins. The reaction was stirred for 2 h at −70° C. DDQ (0.068 g, 3 mmol) in 7 mL of THF was added and the mixture warmed to 25° C. The solvent was removed in vacuo and the residue was purified by silica gel chomatography using CH2Cl2 as the eluent to give compound 773A (0.15 g, 42%) as a red oil.

Provenance & Evidence