Acetic Acid → 6-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 596674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596674
[OH2:1].[NH2:2][NH2:3].O[CH:5]([CH2:22][NH:23]C(C)C)[CH2:6][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([CH2:12][CH2:13][C:14]([O:16]C)=O)=O.[C:27](=O)([O-])[O-].[Na+].[Na+].[C:33](O)(=O)[CH3:34]>O>[OH:1][CH:5]([CH:22]([NH2:23])[CH:33]([CH3:34])[CH3:27])[CH2:6][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]1[CH2:12][CH2:13][C:14](=[O:16])[NH:2][N:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 20309568Methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy)benzoyl]propionate

Produkt 1

HCID 706375736-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Hydrazine hydrate (4.65 ml, 0.09 mole) was added to a solution of methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy) benzoyl]propionate (10 g, 0.03 mole) in glacial acetic acid (80 ml) and the solution was heated under reflux for one hour. Evaporation under reduced pressure gave an oil (25.5 g.) which was dissolved in water, treated with an excess of sodium carbonate solution and extracted with dichloromethane. Evaporation of the dried extracts gave an oil (10.3 g.) which was purified on a silica column by elution with a mixture of chloroform and methanol to give 6-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone (6.25 g, 66%), m.p. 124°-126° C. The hydrochloride, crystallised from 2-propanol, had m.p. 162°-164.5° C.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureunder reflux for one hour
  3. customEvaporation under reduced pressure
  4. customgave an oil (25.5 g.) which
  5. extractionextracted with dichloromethane
  6. customEvaporation of the dried extracts
  7. customgave an oil (10.3 g.) which
  8. customwas purified on a silica column by elution with a mixture of chloroform and methanol

Quellen und Nachweise

ORD-Eintrag
ord-64961a1066dd40faad930610a01e088c
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011321

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