Sodium Hydroxide → HCID 58476273, compound

Participants

Reaction Steps

To a solution of methyl 2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (216 mg, 0.52 mmol) in methanol (8 mL) and tetrahydrofuran (8 mL) was added a 1 M solution of sodium hydroxide (7.87 mL). The mixture was stirred and heated to reflux for 1.5 h. The mixture was concentrated, dissolved in water and acidified to pH=4 with 1M hydrochloric acid. The precipitated solid was filtered and redissolved in tetrahydrofuran, and the organic layers were dried over anhydrous magnesium sulfate. After evaporation of the organic solvent, the residue was treated with dichloromethane to afford 60 mg of 2-(3-(2-carboxypropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Isolated yield: 30%; MS (ESI+APCI) M+1=384.

Provenance & Evidence