Hydrochloric Acid → 2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxylate (606 mg, 1.75 mmol) and LiOH (168 mg, 7.00 mmol) in dioxane/H2O (6 mL/5 mL) was stirred at 80° C. for 2 hours. The reaction was monitored using TLC. When the reaction was completed, 1 N HCl aqueous was added to the mixture until pH 4. The mixture was extracted with EtOAc (10 mL*3). The combined organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated under reduce pressure, afforded 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxylic acid (590 mg, yield: 99%). 1H-NMR (400 MHz, DMSO-d6) δ 7.74 (d, J=8.8 Hz, 1H), 7.43˜7.56 (m, 2H), 7.37 (s, 1H), 7.25˜7.34 (m, 1H), 7.15 (s, 1H), 6.92˜7.02 (m, 1H). MS (M+H)+: 319.

Provenance & Evidence