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Hydrochloric Acid → 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 452622
Notes
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Reaction equation

HRID 452622 reaction equation
C([N:4]1[C:8]2[N:9]=[CH:10][CH:11]=C(C#N)[C:7]=2[CH:6]=[CH:5]1)(=O)C.[OH-:15].[Na+].[CH2:17]([OH:19])[CH3:18].Cl>O>[NH:4]1[C:8]2[N:9]=[CH:10][CH:11]=[C:18]([C:17]([OH:15])=[O:19])[C:7]=2[CH:6]=[CH:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 219614211-Acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962Water

Conditions

Temperature
90 °C

Procedure

A mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (1.80 g, 11.10 mmol), 2 M aqueous sodium hydroxide solution (25 mL) and ethanol (25 mL) was stirred at 90° C. for 16 hr. The reaction mixture was neutralized with hydrochloric acid and diluted with water. The precipitate was collected by filtration, and washed with water and diethyl ether to give the title compound (1.51 g, yield 84%) as pale-yellow crystals.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-0225558ae596489fab4eb4960642631b
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492378B2

Reaction notes

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