Sodium Hydroxide → 9H-Pyrido[3,4-b]indole-1-carboxylic acid

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Reaction Steps

In 30 ml of methanol was dissolved 0.5 g of 1-carbomethoxy-9H-pyrido[3,4-b]indole and to this solution was added 2 ml of 10% aqueous sodium hydroxide. The mixture was refluxed at water bath temperature for 6 hours, the methanol removed by distillation, the residue neutralized with 10% hydrochloric acid and the resultant crystals recovered by filtration. Recrystallization from methanol yields 350 mg of 1-carboxy-9H-pyrido[3,4-b]indole as colorless needles, m.p. 239°-240° C. (decomp.). Mol. wt. (based on mass spectrum) 212. The IR absorption spectrum shows absorption at 1680 cm-1 in the starting compound has disappeared and, instead, an absorption of the carboxyl group is observed at 1580-1600 cm-1.

Provenance & Evidence