Sodium Hydroxide → 1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid

HRID 1693351Notes

Reaction equation

HRID 1693351 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:16][C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[CH:9]=1)=[O:7])C>C(O)C>[NH:16]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[CH:9]=[C:8]1[C:6]([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44630701Ethyl 1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Product 1

HCID 176088121H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide solution (2.4 mL, 2M, 4.8 mmol) was added to a solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (Preparation 11, 0.76 g, 4.0 mmol) in ethanol (40 mL) and the mixture heated under reflux for 2 h before being cooled and concentrated in vacuo. The residue was dissolved in a minimum amount of water, glacial acetic acid (1 mL) was added and the solution cooled in a refrigerator for 3 days. The resultant precipitate was collected by filtration washed with ether and dried in vacuo to give the title compound as a cream coloured solid. δH (D2O): 7.05 (1H, s), 7.63 (1H, d), 8.08 (1H, d), 8.94 (1H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 h
  3. temperaturebefore being cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in a minimum amount of water, glacial acetic acid (1 mL)
  6. additionwas added
  7. temperaturethe solution cooled in a refrigerator for 3 days
  8. filtrationThe resultant precipitate was collected by filtration
  9. washwashed with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-3904bc93322d4a049eced7bfb300e4ee
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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