Sodium Hydroxide → 3,3-Dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

To a mixture of methyl 3,3-dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (90 mg, 0.21 mmol) in methanol (3 mL) and water (1.5 mL) was added a solution of sodium hydroxide (143 mg, 3.57 mmol.) in water (1.5 mL). The resultant mixture was heated to reflux until the completion 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 3,3-dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid, 75 mg, Yield 85% MS (ESI+APCI) M+1=415.6.

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