Hydrazine hydrate (1:1) → 6-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one

HRID 2168622

Reaktionsgleichung

C([O:3][C:4](=O)[CH:5](O)[CH:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)[C:7](=O)[CH2:8][CH2:9][CH2:10][CH3:11])C.O.[NH2:29][NH2:30]>C(O)(=O)C>[CH2:8]([C:7]1[C:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][CH:14]=2)=[CH:5][C:4](=[O:3])[NH:29][N:30]=1)[CH2:9][CH2:10][CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a stirred solution of the octanoic acid ethyl ester (105 mmol, 39.5 g) in glacial acetic acid (25.5 mL) was added hydrazine hydrate (525 mmol, 25.5 mL), and the reaction was heated at 100° C. for 12 h. After cooling, the volatiles were removed in vacuo, the residue was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), saturated NaHCO3 (3×100 mL), brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate (200 mL) and hexanes (300 mL) to afford 6-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one.

Aufarbeitung

temperatureAfter cooling
customthe volatiles were removed in vacuo
dissolutionthe residue was dissolved in ethyl acetate (300 mL)
washThe organic layer was washed with water (100 mL), saturated NaHCO3 (3×100 mL), brine (100 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from a mixture of ethyl acetate (200 mL) and hexanes (300 mL)

Quellen und Nachweise

ORD-Eintrag: ord-883f1ece877845ae8e7c194509903f03
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09045461B2

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