Sodium Bicarbonate → HCID 18617490, compound

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Reaction Steps

A solution of methyl 4-(2-cyano-pyridin-4-yl)-benzoate (400 mg, 1.68 mmol) (reference example 57) in 80% sulphuric acid (3 mL) is stirred at room temperature for 12 hours. The resulting solution is poured onto ice and the mixture brought to pH 8 with sat. sodium bicarbonate solution then extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 40% ethyl acetate in chloroform) to give 340 mg of the title compound. 1H NMR (CDCl3) δ 3.94 (s, 3H), 5.72 (bs, 1H), 7.67 (dd, J=5, 1 Hz, 1H), 7.75 (d, J=8 Hz, 2H), 7.9 (bs, 1H), 8.15 (d, J=8 Hz, 2H), 8.46 (bs, 1H), 8.63 (d, J=5 Hz, 1H). MS (EI) m/z 256.

Provenance & Evidence