Hydrochloric Acid → HCID 44600573, compound

Participants

Reaction Steps

To a solution of methyl isonicotinate (540 mg, 3.94 mmol) in dry acetone (5 mL) was added 1-iodobutane (1.35 mL, 11.8 mmol) followed by toluene (1 mL). The reaction mixture was stirred at ambient temperature for 3 h and then heated to 50° C. over night. Acetonitrile (5 ml) was added and the temperature was raised to 80° C. for 5 h. The reaction mixture was allowed to cool to ambient temperature and was stirred over the week end. The solvent was removed in vacuo and the crude was purified by column chromatography using a gradient of methanol in dichloromethane with 1% acetic acid. 615 mg of the intermediate product was dissolved in water (6 mL) and dropwise added a 10 M solution of sodium hydroxide (1.149 mL, 11.49 mmol) and a 1.25 M solution of potassium ferricyanide(III) (3.06 mL, 3.83 mmol) in hot water over 2 h. The reaction mixture was stirred at ambient temperature for 4 h. 3M hydrochloric acid was added until an acidic pH was reached. The reaction mixture was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate and concentrated in vacuo to yield 235 mg (40% total yield) of the title compound as a solid; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.78 (d, 1 H), 6.82 (d, 1 H), 6.53 (dd, 1 H), 3.89 (t, 2 H), 1.52-1.65 (m, 2 H), 1.18-1.34 (m, 2 H), 0.89 (t, 3 H); MS (ESI) m/z 196[M+H+], m/z 194[M−H+].

Provenance & Evidence