Sodium Hydroxide → 1H-Pyrrolo(2,3-c)pyridine-2-carboxylic acid

HRID 1693354Notes

Reaction equation

HRID 1693354 reaction equation
C([O:3][C:4]([C:6]1[NH:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[NH:14]1[C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21819001ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 218190021H-Pyrrolo(2,3-c)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (Preparation 14, 310 mg, 1.6 mmol) in ethanol (20 mL) was added 2N sodium hydroxide solution (1 mL, 2.0 mmol) and the reaction mixture heated under reflux for 1.5 h then concentrated in vacuo. The residue was dissolved in water (10 mL) and acidified with acetic acid giving an immediate brown precipitate. The solid was filtered and dried to give the title compound as a beige solid. δH (D2O): 7.11 (1H, s), 7.99 (1H, d), 8.05 (1H, d), 8.85 (1H, s); m/z (ES+)=163 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 1.5 h
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in water (10 mL)
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-c577ff193f37403494e70f1364ae0733
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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