Water → HCID 57983519, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethyl 5-hydroxy-7-imino-8,8-dimethyl-7,8-dihydroquinoline-6-carboxylate (100 mg, 384 μmol) and water (3 mL, 166525 μmol), was added H2SO4 (0.02 mL, 384 μmol). The resulting mixture was then heated to 80° C. After 30 minutes, 0.1 mL of H2SO4 was added. After 90 minutes, the reaction was cooled to room temperature and extracted with EtOAc. The organic phase was washed with water and then with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give a light-yellow solid. The aqueous layer was concentrated in vacuo to give a white solid/yellow liquid. The solid was washed with EtOH and a white solid was filtered away. The filtrate was concentrated in vacuo to give a yellow solid. The solid was washed with DCM and the supernatant was decanted off. The solid was dissolved in MeOH and concentrated in vacuo to give a light-yellow solid which was washed once more with DCM and the supernatant was decanted away. The solid was placed under high-vacuum to leave a light-yellow solid which was purified by silica flash chromatography (0-10% MeOH/DCM) to give the title compound as a white crystalline solid (24 mg, 24%). MS (m/z)=262 (M+H)+. Calculated for C14H15NO4 261.3.

Provenance & Evidence