Hydrochloric Acid → HCID 58476128, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,3-dimethyl-2-[3-(1-methyl-ureido)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (190 mg, 0.5 mmol) in methanol (5 mL) and tetrahydrofuran (10 mL), 30% sodium hydroxide in water (10 mL) was stirred at 60° C. for 36 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 3,3-dimethyl-2-[3-(1-methyl-ureido)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (28 mg, 15%) as a white solid: LC/MS m/e calcd for C20H23N3O3 (M+H)+: 354.42, observed: 354.1.

Provenance & Evidence