Sodium Hydroxide → 1H-Pyrazolo(4,3-b)pyridine-6-carboxylic acid

HRID 711054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711054
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12]C)=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+]>CO.O>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[N:2]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 60144275Methyl 1H-pyrazolo[4,3-B]pyridine-6-carboxylate

Produkt 1

HCID 671513391H-Pyrazolo(4,3-b)pyridine-6-carboxylic acidAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 1H-pyrazolo[4,3-b]pyridine-6-carboxylate (3.52 g, 20 mmol) in methanol (250 mL) and water (190 mL) at 0° C. was added aqueous sodium hydroxide (2M, 64 mL, 128 mmol), dropwise. The suspension was then allowed to warm to ambient temperature and stirred for 18 hours. The methanol was then removed in vacuo and the aqueous mixture extracted with ethyl acetate (250 mL). The aqueous layer was acidified (to pH 5-6) with 2 N aqueous hydrochloric acid (70 mL). The cream solid which had precipitated out was then filtered off and dried in a desiccator to yield the title compound (0.675 g, 21%). 1HNMR (400 MHz, DMSO-d6, δ): 8.97 (s, 1H), 8.45 (s, 1H), 8.39 (s, 1H).

Aufarbeitung

  1. customThe methanol was then removed in vacuo
  2. extractionthe aqueous mixture extracted with ethyl acetate (250 mL)
  3. customThe cream solid which had precipitated out
  4. filtrationwas then filtered off
  5. customdried in a desiccator

Quellen und Nachweise

ORD-Eintrag
ord-1806240758984cd28199493b90daadf6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181252B2

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