2-Methoxyaniline → o-[2-Ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole

HRID 2379426노트

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HRID 2379426 반응식
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][C:13](=[O:24])[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:11].[CH:25](OCC)(OCC)OCC>C(O)C>[CH2:10]([O:12][C:13]([CH:14]([C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:25]=[N:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:24])[CH3:11]

참가 물질

5

반응물 3

HCID 70002-MethoxyanilineHCID 31214Ethyl orthoformateHCID 81576Diethyl 3-oxoadipate

생성물 1

HCID 18957128o-[2-Ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole수율 82%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
20 °C

실험 절차

A mixture consisting of 5.0 g (0.041 mole) of o-anisidine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.), 8.86 g (0.041 mole) of β-ketoadipic acid diethyl ester (available from Sigma Chemical Company of St. Louis, Mo.) and 6.07 g (0.041 mole) of triethyl orthoformate (also available from Aldrich) was placed in an open reaction flask and heated to 140° C. for a period of three hours, at which point no further amount of ethanol by-product formation could be observed to evolve from the reaction mixture. Upon completion of this step, the spent reaction mixture was allowed to cool to ambient temperatures (ca. 20° C.) on standing overnight for a period of approximately 16 hours. The resulting residual solid was thereafter triturated with petroleum ether and filtered to give 11.53 g (82%) of pure o-[2-ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole. The pure product was characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data.

후처리

  1. customUpon completion of this step, the spent reaction mixture
  2. customThe resulting residual solid was thereafter triturated with petroleum ether
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-b8da32933a734eab98d21aeccba739b2
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05362743

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