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

HRID 973710

Reaction equation

HRID 973710 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

HCID 13086AmeltolideYield 49.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-bbb4122addcf4ee4a9059072a39d054a
Source dataset
uspto-grants-1991_11
Patent number
US05064862

Linked notes

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