Dimethylformamide → HCID 57803016, compound

Participants

Reaction Steps

To a mixture of 5-hydroxy-N-methylpyridine-2-carboxamide (400 mg, 3.0 mmol), 1,3-propanediol (230 mg, 3.0 mmol), triphenylphosphine (786 mg, 3.0 mmol) and N,N-dimethylformamide (4.5 ml, 60 mmol) was added diisopropyl azodicarboxylate (606 mg, 3.0 mmol) while stirring at ambient temperature. After 18 hours, the solvent was removed under reduced pressure and the resulting residue was taken up in ethyl acetate (40 mL) and filtered. The filtrate was concentrated and purified by column chromatography over silica gel using methanol/ethyl acetate (3-4%) to give 488 mg (80%) of 5-(3-hydroxypropoxy)-N-methylpyridine-2-carboxamide as a colorless gum. MS [M+H] 211.2, 1H NMR (CDCl3) δ (ppm) 8.19 (d, J=3.0 Hz, 1H), 8.13 (d, J=8.7 Hz, 1H), 7.83 (b, 1H), 7.28 (m, 1H), 4.21 (t, J=6.3 Hz, 2H), 3.88 (m, 2H), 3.02 (d, J=5.1 Hz), 2.08 (m, 2H).

Provenance & Evidence