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

HRID 1362929Notes

Reaction equation

HRID 1362929 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

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (Preparation 7, 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 was 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 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 was 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-6d34548af9cc40c8a3f792fc08de4d80
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

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