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

HRID 973710

반응식

HRID 973710 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 13086Ameltolide수율 49.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-bbb4122addcf4ee4a9059072a39d054a
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064862

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