Sodium Hydroxide → 4-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

HRID 733723Notes

Reaction equation

HRID 733723 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:14]([CH3:15])[CH:13]=[CH:12][C:7]=2[C:8]([Cl:11])=[N:9][CH:10]=1)=[O:4].[OH-].[Na+]>CO>[Cl:11][C:8]1[C:7]2[CH:12]=[CH:13][N:14]([CH3:15])[C:6]=2[C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44475508Methyl 4-chloro-1-methyl-1H-pyrrolo(3,2-c)pyridine-7-carboxylate

Product 1

HCID 578409034-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester (0.5 g), in methanol (20 ml) was added aqueous 2M sodium hydroxide solution (2 ml) and the mixture was heated to reflux for 4 hours. The methanol was evaporated and the residue was dissolved in water (50 ml) and acidified to pH 1 using aqueous 2M hydrochloric acid. Solid sodium chloride was added to saturated the aqueous phase, the solution was extracted with tetrahydrofuran (2×50 ml). The tetrahydrofuran layers were combined and evaporated to afford the title compound (460 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe methanol was evaporated
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. additionSolid sodium chloride was added to saturated the aqueous phase
  6. extractionthe solution was extracted with tetrahydrofuran (2×50 ml)
  7. customevaporated

Sources & evidence

ORD record
ord-fe0c20e70d014f5980cabd7cc0e0d41e
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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