Benzene → HCID 178498115, compound

Participants

Reaction Steps

2-Hydroxynicotinic acid (6.95 g, 50 mmol) was dissolved in 125 mL of methanol, 75 mL of benzene, and 0.75 mL of concentrated sulfuric acid under nitrogen and heated at reflux for 2.5 hours. A Dean-Stark trap was added to the apparatus and heating was continued overnight. The volatiles were removed under reduced pressure and the resulting solid was suspended in cold water (150 mL) and filtered to remove unreacted starting material. The filtrate was extracted with methylene chloride and chloroform. The combined organic extracts were concentrated in vacuo to afford 2.5 g. Recrystallization from hot benzene afforded 1.7 g (22%) of the title compound. 1H NMR (CD3OD, 300 MHz) δ 3.83 (s, 3H), 6.45 (t, 1H), 7.68 (dd, 1H), 8.29 (dd, 1H). MS (DCl/NH3) m/e 154 (M+H)+.

Provenance & Evidence