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

HRID 2064249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064249
[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) before being acidified (to pH 5-6) with aqueous hydrochloric acid (2 M, 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, 4.16 mmol, 21% yield). 1HNMR (400 MHz, DMSO-d6): δ ppm 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-45d22d6003a54f37b0fda8125bba1bc2
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288405B2

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