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

HRID 1733225Notes

Reaction equation

HRID 1733225 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5972669H-Pyrido(3,4-b)indole-1-carboxylic acid, methyl ester

Product 1

HCID 155730799H-Pyrido[3,4-b]indole-1-carboxylic acidYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. temperatureThe mixture was refluxed at water bath temperature for 6 hours
  2. customthe methanol removed by distillation
  3. filtrationthe resultant crystals recovered by filtration
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f32af372a8c94b8b9e559fa20fe71e33
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

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