Hydrochloric Acid → 5-(Ethoxycarbonyl)pyridine-3-carboxylic acid

Participants

Reaction Steps

To a solution of 10 g (0.045 mol) of compound 6 in 75 ml of ethyl alcohol, 25 ml of 2N alcoholic KOH was added while stirring. Stirring was continued for 1/2 hr at room temperature. To the mixture 12.5 ml of 4N HCl was added while stirring. The solid separated was filtered and washed with alcohol. The combined filtrate and washings were distilled on rotovap and the residue was washed with water, filtered and crystallized from ethanol. Yield 7.5 g (86%), m.p. 180°-182°, NMR (CDCl3 /DMSO-d6) δ10.56 (bs, 1H, COOH), 9.26 (d, 2H, J=2 Hz, C2 and C6 pyridine protons), 8.75 (t, 1H, J=2 Hz, C4 pyridine protons), 4.4 (q, 2H, J=7 Hz, O--CH2), 1.42 (t, 3H, J=7 Hz, CH3).

Provenance & Evidence