Sodium Hydroxide → 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 751614Notes

Reaction equation

HRID 751614 reaction equation
C([O:3][C:4]([C:6]1[NH:15][C:9]2=[CH:10][N:11]=[C:12]([Cl:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:14][C:12]1[CH:13]=[C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[NH:15][C:9]2=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44630703Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Route A: To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (Preparation 17, 1.78 g, 7.9 mmol) in ethanol (70 mL) was added sodium hydroxide solution (5.2 mL, 2M, 10.3 mmol) and the mixture heated under reflux for 2 h. The solvent was removed in vacuo and the solid dissolved in water (150 mL) and acidified to pH 4 with acetic acid to give the title compound as a brown solid that was isolated by filtration. δH (CD3OD): 7.13 (1H, s), 7.68 (1H, s), 8.58 (1H, s); m/z (ES+)=197 [M+H]+.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe solid dissolved in water (150 mL)

Sources & evidence

ORD record
ord-77df3db9059c4a93a2a686424e9dc451
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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