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

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Reaction Steps

A mixture of methyl 2-(4-benzamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (67 mg, 0.16 mmol) in methanol (8 mL) and aqueous sodium hydroxide solution (1 M, 1.2 mL, 1.2 mmol) was heated to reflux for 5 h, LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 2 M hydrochloric acid solution until lots of yellow solid precipitated, which was collected by filtration to afford 51 mg of 2-(4-benzamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid in 80% yield. MS (ESI+APCI) M+1=401.

Provenance & Evidence