Ethyl Acetate → HCID 67441465, compound

Participants

Reaction Steps

Methyl 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg, 0.32 mmol) and sodium hydroxide (0.2 g, 5 mmol) was dissolved in methanol/water (10 mL/2 mL) and the reaction mixture was allowed to reflux for 1.5 h. Thin layer chromatography (petroleum ether:ethyl acetate=3:1, Rf=0.1) showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 1 M hydrochloric acid solution to pH=6. The precipitated off-white solid was collected by filtration and dissolved in 50 ml of acetone, dried over sodium sulfate. Filtered and concentrated, the residue was recrystallization from dichloromethane/hexane to afford 78 mg of 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, Yield: 82.1%, MS (ES+APCI) M+1=297.1.

Provenance & Evidence