Potassium Hydroxide → 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 1821805Notes

Reaction equation

HRID 1821805 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([O:13]CC)=[O:12])[NH:8][C:7]=12.[OH-].[K+]>O1CCCC1.CO>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[NH:8][C:7]=12

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 46839972Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 768529167-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.64 g, 2.85 mmol) was dissolved in tetrahydrofuran (5.7 mL) and methanol (6.8 mL). To the mixture was added 3 N KOH (2.85 mL). After stirring overnight (15.5 h) at room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in water. This aqueous solution was made acidic (pH 3) using 6 N HCl. The precipitate was collected by filtration. The precipitate was dissolved in methanol and concentrated to dryness to afford 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (0.53 g, 2.7=mmol, 94%) as a yellow powder: mp 210-214° C.; 1H NMR (300 MHz, CD3OD) δ7.25 (1H, s), 7.65 (1H, d, J=5.4 Hz), 7.94 (1H, d, J=5.4 Hz); ESI MS m/z 195 [C8H5ClN2O2—H]−; HPLC (Method A) >99% (AUC), tR=12.2 min.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in water
  3. filtrationThe precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in methanol
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d296640081d842e2a1fed356f4210d6b
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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