N-(2,6-Dimethylphenyl)-4-nitrobenzamide → Ameltolide

HRID 973710

Reaktionsgleichung

Reaktionsgleichung von HRID 973710
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])=[O:9])=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 477704N-(2,6-Dimethylphenyl)-4-nitrobenzamide

Produkt 1

HCID 13086AmeltolideAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5.0 g of 4-nitro-N-(2,6-dimethylphenyl) benzamide in 250 ml of ethanol was added to a Paar hydrogenation bottle along with 250 mg of 5% palladium on carbon. The mixture was subjected to low pressure hydrogenation (45 psi) for three hours. The mixture was filtered through celite and the filtrate was evaporated in vacuo. The resulting residue was purified by (crystallization from benzene-petroleum ether) [column chromatography over silica gel using a step-wise solvent gradient of petroleum ether and diethyl ether] to provide 2.2 g of the desired title product, m.p. 212°-215° C.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate was evaporated in vacuo
  3. customThe resulting residue was purified by (crystallization from benzene-petroleum ether) [column chromatography over silica gel using a step-wise solvent gradient of petroleum ether and diethyl ether]

Quellen und Nachweise

ORD-Eintrag
ord-bbb4122addcf4ee4a9059072a39d054a
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064862

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