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

HRID 1821805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821805
[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

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 46839972ethyl 7-chloro-1H-pyrrolo(2,3-c)pyridine-2-carboxylate

Produkt 1

HCID 768529167-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acidAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d296640081d842e2a1fed356f4210d6b
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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