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2-Morpholinoethylamine → 7-{[2-(4-Morpholinyl)ethyl]amino}-6-nitro-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

HRID 2213747
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HRID 2213747 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:20]#[N:21])=[CH:8][N:9]2[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[NH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(#N)C>[N:29]1([CH2:28][CH2:27][NH:26][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:20]#[N:21])=[CH:8][N:9]3[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:4][C:3]=2[N+:23]([O-:25])=[O:24])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 4082852-MorpholinoethylamineHCID 102711017-Chloro-6-nitro-4-oxo-1-([2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

생성물 1

HCID 219564797-{[2-(4-Morpholinyl)ethyl]amino}-6-nitro-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile수율 62%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1.25 g (3.29 mmol) of 7-chloro-6-nitro-4-oxo-1-{[2-(trimethylsilyl)-ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile and 1.07 g (8.2 mmol) of 4-(2-aminoethyl)-morpholine in 21 mL of acetonitrile is heated at reflux temperature for 17 hours. After cooling, the mixture is concentrated under reduced pressure and the residue is partitioned between methylene chloride and brine. The separated organic layer is dried over sodium sulfate and filtered. Removal of the solvent yields a residue which is flash chromatographed (elution with methylene chloride, then a gradient of 99:1 to 98:2 methylene chloride/methanol), giving 966 mg (61.9%) of the product as a yellow solid, mp 294–216° C.

후처리

  1. temperatureis heated
  2. temperatureat reflux temperature for 17 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated under reduced pressure
  5. customthe residue is partitioned between methylene chloride and brine
  6. dry with materialThe separated organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customRemoval of the solvent
  9. customyields a residue which
  10. customchromatographed (
  11. washelution with methylene chloride

출처 및 근거

ORD 기록
ord-a6fe9d329c384fceb01b5b493d22dc33
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07105531B2

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