Hydrazine hydrate (1:1) → 6-[4-(3-aminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 1590788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590788
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 144418626-[4-(3-phthalimidopropyloxy)phenyl]-4,5-dihydro3(2H)-pyridazinone

Produkt 1

HCID 144418676-[4-(3-aminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinoneAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2.748 g (7.28 mmol) of the phthalimide prepared above and 398 microliters (8.0 mmol) of 98% hydrazine hydrate in 75 ml of ethanol is heated overnight at reflux under N2. After cooling to RT, the volatiles are removed under vacuum. The residual white solid is taken up in 15 ml of 70:30 CH3OH:NH4OH and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH) to give 929 mg of 6-[4-(3-aminopropyloxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone as a white solid. Yield, 23%.

Aufarbeitung

  1. temperatureis heated overnight
  2. temperatureat reflux under N2
  3. customthe volatiles are removed under vacuum
  4. customNH4OH and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-e9ff8ea5e36f450da85ee61d73f91d36
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204463

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