N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide → N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 380788

Reaktionsgleichung

[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])=[C:4]([F:22])[CH:3]=1>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])[CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A mixture of N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (10.6 g, 32.7 mmol) in acetic acid is heated to 65° C., treated portionwise with iron powder (7.30 g, 130.7 mmol) over 40 minutes, stirred for 10 minutes, and filtered through diatomaceous earth. The resultant filtrate is washed with ethyl acetate, concentrated in vacuo, diluted with ethyl acetate and saturated sodium hydrogen carbonate solution, and filtered through a filter pad. The phases are separated and the organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow solid (8.94 g, 94% yield, mp 164-165° C.).

Aufarbeitung

filtrationfiltered through diatomaceous earth
washThe resultant filtrate is washed with ethyl acetate
concentrationconcentrated in vacuo
additiondiluted with ethyl acetate and saturated sodium hydrogen carbonate solution
filtrationfiltered through a filter pad
customThe phases are separated
washthe organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-e2fd22ce45a94842b667fb8d90cb3450
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06303783B1

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