Acetic Acid → 5-Methoxy-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester (Preparation 35, 128 mg, 0.58 mmol) in ethanol (10 mL, absolute) was added aqueous sodium hydroxide (0.35 mL, 2M) and the mixture heated to 70° C. for 3 h then cooled to rt. The solution was adjusted to pH 4 by addition of glacial acetic acid and the solvents removed under reduced pressure. Ethyl acetate (20 mL) was added to the resulting oil and the mixture sonicated until a fine suspension formed. The mother liquor was decanted and the remaining solid was washed with ethyl acetate and dried in vacuo to give the title compound as a pale orange powder. δH (CD3OD): 3.92 (3H, s), 6.63 (1H, d), 6.94 (1H, s), 7.72 (1H, d).

Provenance & Evidence