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Water → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

HRID 1593783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1593783
[C:1]([C:3](=[CH:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])=[C:21]([I:30])[CH:20]=1)[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=O)#[N:2].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:16][C:8]1[CH:9]=[C:10]([Cl:15])[C:11]([O:13][CH3:14])=[CH:12][C:7]=1[NH:6][C:4]1[C:24]2[C:19](=[CH:20][C:21]([I:30])=[C:22]([O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:23]=2)[N:18]=[CH:17][C:3]=1[C:1]#[N:2]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride3×HCID 693123182-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide

Produkt 1

HCID 115847334-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrileAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide (1.0 g, 1.80 mmol) in 35 mL of toluene was heated to reflux and phosphorous oxychloride (1.7 mL, 18.0 mmol) was added dropwise. The mixture was heated at reflux for 2 hours, and an additional 1.7 mL of phosphorous oxychloride was added. The mixture was continued to heat at reflux for 2 hours, and an additional 1.7 mL of phosphorous oxychloride was added and the reaction mixture was heated at reflux overnight. The reaction is then cooled to room temperature and water was added followed by 10 N sodium hydroxide. The mixture was stirred in an ice-bath for 30 minutes and the precipitate was collected by filtration, washed with methylene chloride to give 870 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-iodo-6-(2-methoxyethoxy)-3-quinolinecarbonitrile as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 3.41 (s, 3H), 3.81 (t, 2H), 3.87 (s, 3H), 4.34 (t, 2H), 7.40 (s, 1H), 7.78 (s, 1H), 7.88 (s, 1H), 8.43 (s, 1H), 8.45 (s, 1H), 9.85 (s, 1H); MS (ES) m/z542.1, 544.1 (M−H)−

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperatureto heat
  6. temperatureat reflux for 2 hours
  7. temperaturethe reaction mixture was heated
  8. temperatureat reflux overnight
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-54a225f9798244bbba87f9588ea8649b
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07297795B2

Notizen zur Reaktion

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