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1-Bromopropane → 1-Propyl-1h-indazole-3-carboxylic acid

HRID 1586452
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1586452
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[H-].[Na+].Br[CH2:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1)[CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 78250Indazole-3-carboxylic acid

Produkt 1

HCID 106320111-Propyl-1h-indazole-3-carboxylic acidAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1H-indazole-3-carboxylic acid (5.00 g) in DMF (40 ml) was gradually added 60% sodium hydride (1.55 g) at 0° C. with stirring, and the mixture was stirred at room temperature for one hour. Then 1-bromopropane (4.55 g) was added, and the mixture was stirred overnight. The reaction solution was distilled off, dissolved in water, and washed with ethyl acetate. The aqueous layer was made acidic with hydrochloric acid, extracted with ethyl acetate, then the extract was dried over anhydrous magnesium sulfate, and decolorized with active carbon. After the solvent was distilled off, crystallization from ether gave the title compound (4.24 g) as crystals. Yield=67%.

Aufarbeitung

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for one hour
  3. stirringthe mixture was stirred overnight
  4. distillationThe reaction solution was distilled off
  5. dissolutiondissolved in water
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customcrystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-738ee3fc61c6471c95a8397993440009
Quelldatensatz
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05945434

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