Sodium Hydroxide → (3-Bromoquinolin-6-yl)acetic acid

Participants

Reaction Steps

A mixture of (3-bromo-quinolin-6-yl)-acetic acid methyl ester (14.8 g, 52.8 mmol) and aqueous 2 N NaOH (80 ml, 160 mmol) was heated under reflux for 1.5 hours until reaction mixture became clear. After cooling down to room temperature the reaction mixture was washed with dichloromethane then the water layer was acidified with concentrated hydrochloric acid to pH 4. A white precipitate was filtered off the stirred in refluxing methanol, filtered and dried in vacuo to give the product title compound as a white solid (10.3 g, 73.5%). (300 MHz, DMSO-d6): 12.52 (b, 1H), 8.91 (d, 1H), 8.69 (d, 1H), 7.99 (d, 1H)), 7.82˜7.70 (m, 2H), 3.80 (s, 2H). ES-MS m/z: 266 (M+H+).

Provenance & Evidence