4-Methylpiperidine → 6'-Chloro-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

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Reaction Steps

A flask was charged with 2,6-dichloro-3-nitropyridine (1.00 g, 5.00 mmol), absolute ethanol (25 mL), and 4-methylpiperidine (0.65 mL, 5.5 mmol) and stirred 15 h at RT. The solvents were removed in vacuo and purification of the resulting residue by silica gel preparative TLC eluting with 10% ethyl acetate in hexane yielded 577 mg (45%) of the title compound as a yellow glass. LC-MS (ESI, m/z): Calcd. for C11H15ClN3O2, 256.1/258.1 (M+H); found: 256.1/258.1.

Provenance & Evidence