Dimethylformamide → 7-(Benzyloxy)-4-chloro-3-nitroquinoline

HRID 419288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419288
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.P(Cl)(Cl)([Cl:30])=O>O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:30])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178526778HCID 178526778, Verbindung

Produkt 1

HCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 2-liter round bottom flask was charged with 7-(benzyloxy)-3-nitroquinolin-4-ol (100.0 g, 0.3 mol) and N,N-dimethylformamide (DMF) (650 mL). Phosphorous oxychloride (62.1 g, 37.7 mL, 1.2 equivalents (eq)) was slowly added dropwise. The resulting mixture was heated at 100° C. for 10 minutes, and then allowed to cool to 39° C. The reaction mixture was poured over ice (3 L). A brown precipitate formed. The mixture was diluted with water (1 L) and stirred to break up the precipitate. The precipitate was collected by vacuum filtration. The filter cake was washed with water (2 L) and air-dried on vacuum filter for 1 hour. The solid was dissolved in dichloromethane and placed in a separatory funnel. The water was removed, and the dichloromethane solution was dried over magnesium sulfate. The solution was then filtered through filter agent to provide a solution of 7-(benzyloxy)-4-chloro-3-nitroquinoline in dichloromethane (approximately 1700 mL).

Aufarbeitung

  1. temperatureto cool to 39° C
  2. customA brown precipitate formed
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washThe filter cake was washed with water (2 L)
  5. customair-dried on vacuum
  6. filtrationfilter for 1 hour
  7. dissolutionThe solid was dissolved in dichloromethane
  8. customplaced in a separatory funnel
  9. customThe water was removed
  10. dry with materialthe dichloromethane solution was dried over magnesium sulfate
  11. filtrationThe solution was then filtered
  12. filtrationthrough filter agent

Quellen und Nachweise

ORD-Eintrag
ord-7861d00bac1c4edf8cf80231ed12f4cf
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093390B2

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