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

HRID 2213747Notes

Reaction equation

HRID 2213747 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a6fe9d329c384fceb01b5b493d22dc33
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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