Hydrochloric Acid → 4-Chloro-1H-pyrrolo(2,3-b)pyridine-5-carboxylic acid

HRID 1696204Notes

Reaction equation

HRID 1696204 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 260764404-Chloro-1H-pyrrolo(2,3-b)pyridine-5-carboxylic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (100 mg) in ethanol (1 mL) was added 1M NaOH solution (0.89 mL) and the mixture was stirred at 50° C. for 2 hours. The mixture was cooled to 4° C. and acidified with 1M HCl and the precipitate was filtrated and washed with water to give 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (75 mg) as a white powder.

Workup

  1. temperatureThe mixture was cooled to 4° C.
  2. filtrationthe precipitate was filtrated
  3. washwashed with water

Sources & evidence

ORD record
ord-dc547dcd98934e2ba9704fe5eea667df
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…