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Dimethylamine → N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine

HRID 1014363
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1014363
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[CH3:20][NH:21][CH3:22]>CO>[CH3:20][N:21]([CH3:22])[CH2:3][CH2:2][C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 594418921-Acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 59442063N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (crude from previous reaction, assumed 0.91 mmol) was dissolved in methanol (5 mL), treated with excess dimethyl amine (5.0 mL, 10 mmol, 2 M in THF, Aldrich), and the reaction heated in a sealed tube at 65° C. for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was separated and then back-extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to give N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine which was taken directly to the next step without determination of yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83-1.94 (m, 2 H), 2.18 (bs, 6 H), 2.56-2.71 (m, 4 H), 2.80 (t, J=6.4 Hz, 2 H), 3.71 (t, J=6.0 Hz, 2 H), 3.90 (s, 3 H), 7.20 (s, 1 H), 8.27 (very broad singlet due to amide rotomers, 1 H); ESIMS (M+H)+=308.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe aqueous layer was separated
  5. extractionback-extracted with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1071cd8b86c64c919c8bac6127b07390
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981903B2

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