5-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one → 5-(2-Aminophenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 2121748

Reaktionsgleichung

Reaktionsgleichung von HRID 2121748
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13](=[O:15])[NH:12][N:11]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13](=[O:15])[NH:12][N:11]=1

Komponenten

4

Edukt 1

HCID 3129215-(2-nitrophenyl)-3H-1,3,4-oxadiazol-2-one

Produkt 1

HCID 128581485-(2-Aminophenyl)-1,3,4-oxadiazol-2(3H)-oneAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-nitrobenzoylhydrazine (9.05 g, 0.05 mol) in dioxane (30 mL) was slowly added to a solution of trichloromethyl chloroformate (4.6 mL, 0.04 mol) in dioxane (30 mL) at room temperature. On completion of the addition the reaction was heated to reflux for 4 hours. The solvent was evaporated off and the residue re-crystallised from 96% ethanol (50 mL) to give 7.15 g of the 5-(2-nitrophenyl)-3H-[1,3,4]oxadiazol-2-one. M.p. 157-158° C. A solution of the nitro compound (2 g, 9.7 mmol) in 96% ethanol (25 mL) was hydrogenated over 5% palladium on charcoal to give desired 1.6 g of the desired amine.

Quellen und Nachweise

ORD-Eintrag
ord-7c3f7ce3f7284aa99eff46be58c367b4
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696475B2

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