Water → 6-(3-(Hydroxymethyl)phenylthio)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-(5-cyano-pyridin-2-ylsulfanyl)-benzoic acid (1.25 g, 4.88 mmol) in thionyl chloride (50 mL) and stir. Heat to reflux. After 2 hours, concentrate under reduced pressure to give a residue. Dissolve residue in dioxane (100 mL) and add sodium borohydride (1.85 g, 48.8 mmol). Heat to 50° C. After 2 hours, cool to ambient temperature and add water. Extract with ethyl acetate, combine organic layers, dry with sodium sulfate, filter and concentrate to give the title compound as a yellow oil (670 mg, 57%): 1H NMR (DMSO-d6) δ 4.56 (d, 2H), 5.33 (t, 1H), 7.06 (d, 1H), 7.49 (m, 3H), 7.57 (m, 1H), 8.08 (dd, 1H), 8.82 (dd, 1H).

Provenance & Evidence