Acetic Acid → 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid

HRID 751626Notes

Reaction equation

HRID 751626 reaction equation
C([O:3][C:4]([C:6]1[NH:14][C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])C.C(O)(=O)C>[OH-].[Na+]>[NH:14]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 11579250ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylate

Product 1

HCID 226126701H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester (Preparation 31, 0.34 g, 1.77 mmol) in aqueous sodium hydroxide solution (2M, 10 mL) was heated under reflux for 3 h and the resulting solution was allowed to cool to rt. The pH was adjusted to 4 by addition of glacial acetic acid. Excess acetic acid was removed in vacuo and the resulting suspension cooled to 0° C. and then left standing at rt for 16 h. The resulting beige precipitate was collected by filtration and dried to give the title compound as a beige solid. δH (d6 DMSO): 7.12 (1H, s), 7.23 (1H, dd), 7.79 (1H, d), 8.42 (1H, dd).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customExcess acetic acid was removed in vacuo
  4. temperaturethe resulting suspension cooled to 0° C.
  5. waitleft
  6. filtrationThe resulting beige precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-00c4f83888ea484fa2133cce2df1f967
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

Loading…