Hydrochloric Acid → 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 1925576

Reaction equation

HRID 1925576 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[C:8]2[CH:16]=[CH:15][NH:14][C:9]=2[N:10]=[C:11]([Cl:13])[CH:12]=1)=[O:6].Cl>CO>[Cl:13][C:11]1[CH:12]=[C:7]([C:5]([OH:6])=[O:4])[C:8]2[CH:16]=[CH:15][NH:14][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53413062Methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 533995756-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml round-bottomed flask, 7.5 ml of a 1M aqueous solution of lithium hydroxide are added, at ambient temperature, to a suspension of 527 mg of 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid methyl ester obtained according to the preceding stage, in 15 ml of methanol. After stirring for 2.5 hours at ambient temperature, 7.5 ml of 1N hydrochloric acid are added dropwise. After stirring for ½ hour, the solid is filtered off, washed with 25 ml of water and dried. 475 mg of 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid are obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. stirringAfter stirring for ½ hour
  3. filtrationthe solid is filtered off
  4. washwashed with 25 ml of water
  5. customdried

Sources & evidence

ORD record
ord-30b8c646190946a79f1b611048175ec7
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Linked notes

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