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

HRID 973710

反応式

HRID 973710 の反応式
[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

参加物

4

反応物 1

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

生成物 1

HCID 13086Ameltolide収率 49.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-bbb4122addcf4ee4a9059072a39d054a
出典データセット
uspto-grants-1991_11
特許番号
US05064862

関連ノート

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