Sodium Hydroxide → 2-(Quinolin-6-yl)propanoic acid

Participants

Reaction Steps

2-Quinolin-6-yl-propionic acid methyl ester containing 10% 2-methyl-2-quinolin-6-yl-propionic acid methyl ester (7.7 g, 35.8 mmol) and 2 N aq. NaOH (27 ml) was heated to reflux for 4 hours until the reaction mixture became clear. After cooling to room temperature the mixture was extracted with dichloromethane and the aqueous layer was acidified with concentrated hydrochloric acid to pH 4-5. Ethyl acetate (30 ml) was added and stirred for 10 min, the resulting solid was filtered off to obtain product, which was re-crystallized twice from methanol to return the title compound (5.3 g, 73.7%): 1H NMR 300 MHz (DMSO-d6) δ12.43 (s, 1H), 8.86 (d, 1H), 8.33 (d, 1H), 7.99-7.86 (m, 2H), 7.72-7.49 (m, 2H), 3.92 (q, 1H), 1.48 (d, 3H). ES− MS m/z: 200 [M−H+]−, 400 (dimer).

Provenance & Evidence