Hydrochloric Acid → 2-(4,5-dihydro-1H-thieno[2,3-g]indazol-1-yl)ethanol

HRID 1066880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066880
O=[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C([O:13][CH2:14][CH3:15])=O.Cl.[NH:17]([CH:19](O)C)[NH2:18]>O1CCCC1>[N:18]1([CH2:15][CH2:14][OH:13])[C:2]2[C:10]3[CH:9]=[CH:8][S:7][C:6]=3[CH2:5][CH2:4][C:3]=2[CH:19]=[N:17]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 19013750Hydrazinoethanol

Produkt 1

HCID 211966572-(4,5-dihydro-1H-thieno[2,3-g]indazol-1-yl)ethanolAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a tetrahydrofuran (20 ml) solution containing 2.95 g of potassium tert-butoxy was added dropwise a tetrahydrofuran (10 ml) solution containing 2.00 g of 4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene and 3.89 g of ethyl formate under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. After addition of 26 ml of 1 N hydrochloric acid to the reaction solution, 3.16 g of hydrazinoethanol was added under ice-cooling, and then the mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with methylene chloride, and the organic layers were combined, washed with brine and then dried with anhydrous magnesium sulfate. After removal of the drying agent by filtration, the resulting filtrate was concentrated under a reduced pressure to give 1.56 g of 2-(4,5-dihydro-1H-thieno[2,3-g]indazol-1-yl)ethanol as a pale yellow solid.

Aufarbeitung

  1. temperaturecooling
  2. additionwas added under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionThe reaction solution was extracted with methylene chloride
  6. washwashed with brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe resulting filtrate was concentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-15201330f1684b4c8f0c5e850164034e
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245796B1

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