Sodium Hydroxide → HCID 67439955, compound

Participants

Reaction Steps

To a mixture of methyl 2-(3-acetamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (129 mg, 0.37 mmol) in methanol (10 mL) and water (5 mL) was added with a solution of sodium hydroxide (249 mg, 6.22 mmol) in water (5 mL). The resultant mixture was heated to reflux for 1.5 hours. The methanol was removed under vacuum. The residue was acidified with 2 M hydrochloric acid to pH=5-6. The precipitates were collected by filtration, purified by preparative Thin layer chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to afford 2-(3-acetamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a solid. (41 mg, yield: 33.1%). MS (ES+APCI) M+1=339.1.

Provenance & Evidence