Hydrochloric Acid → 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 1766163Notes

Reaction equation

HRID 1766163 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:24])[C:5]1[CH:6]=[C:7]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]([O:22]C)=[O:21])=[CH:12]2)[CH:8]=[CH:9][CH:10]=1.Cl>O1CCCC1>[CH3:3][N:4]([CH3:24])[C:5]1[CH:6]=[C:7]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]([OH:22])=[O:21])=[CH:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21110081methyl 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 211100511-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.6 cm3 of a 10N sodium hydroxide solution were added to methyl 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 15 cm3 of tetrahydrofuran. After stirring at reflux of the solvent for 48 h, the reaction mixture was acidified with 2 cm3 of 10N hydrochloric acid and then concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, characterized by LC/MS (m/z 282 [MH]+), which was used directly in the following stage.

Workup

  1. temperatureat reflux of the solvent for 48 h
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-b0cc6b0ba60f4bddb982a75c0c6e669e
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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