Sodium Hydroxide → 2-(4-Aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

To a mixture of methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxy late (500 mg, 1.61 mmol) in methanol (10 mL) and water (5 mL) was added a solution of sodium hydroxide (1100 mg, 27.4 mmol) in water (15 mL). The resultant mixture was heated for reflux until the complete of the reaction (monitored by thin layer chromatography). The methanol was removed under vacuum. The residue was acidified with 2 M hydrochloric acid to pH=1. The precipitates were collected by filtration to afford 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid, 430 mg, Yield 94%.

Provenance & Evidence