Hydrazine hydrate (1:1) → 2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

HRID 335402

Reaktionsgleichung

O.[NH2:2][NH2:3].[CH2:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][CH3:14])[C:7]=1[C:15](=[O:21])[C:16](OCC)=[O:17])[CH3:5]>CO>[CH2:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][CH3:14])[C:7]=1[C:15](=[O:21])[C:16]([NH:2][NH2:3])=[O:17])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 2 °C

Versuchsvorschrift

To a 100 ml volume four-necked flask, methanol (22.91 g) and hydrazine hydrate (1.93 g) were added at room temperature, and cooled. Ethyl 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetate (9-a) (5.01 g) diluted with methanol (10.02 g) was added dropwise at 1° C. over 5 minutes. The resulting mixture was stirred at 2° C. for 4 hours, then the mixture was filtered. The resulting filtrate was concentrated, added tert-butyl methyl ether (41 g), and washed with brine (14 g). The resulting organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel: 40 g, hexane:ethyl acetate=1:1) to gave 1.88 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazide ((12-1)-(11)-39).

Aufarbeitung

temperaturecooled
additionwas added dropwise at 1° C. over 5 minutes
filtrationthe mixture was filtered
concentrationThe resulting filtrate was concentrated
additionadded tert-butyl methyl ether (41 g)
washwashed with brine (14 g)
dry with materialThe resulting organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-6a5931a32b8f45f7b72b66bd9ce9b3d1
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08884010B2

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