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1,3-Diethyl 2-oxopropanedioate → Ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 1942158
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HRID 1942158 반응식
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([NH:11][C:12]3[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:10][C:2]1=2.O=[C:20]([C:26](OCC)=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:12]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:18]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]3=[O:27])[CH:9]=[CH:10][C:2]1=2
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참가 물질

4

반응물 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 43148731N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine

생성물 1

HCID 67533036Ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate수율 63%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5.0 g (21 mmol) of N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine and 3.9 g (22 mmol) of diethyl ketomalonate were dissolved in toluene (60 ml), and the solution was heated to reflux for 12 hours while removing water using a Dean-Stark apparatus. The reaction solution was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3) to obtain 4.6 g (yield: 63%) of ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a milky yellow powder.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux for 12 hours
  3. customwhile removing water using a Dean-Stark apparatus
  4. washThe reaction solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3)

출처 및 근거

ORD 기록
ord-f1e0742e619d45bcb131881949db4408
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08389523B2

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