Phosphorus oxychloride → HCID 178486400, Verbindung

HRID 902417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902417
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[CH:3]=1)[NH:11][CH:10]=[C:9]([C:14]#[N:15])[C:8]3=O.P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:8]1[C:7]2[C:12](=[CH:13][C:4]3[CH:3]=[C:2]([OH:1])[C:18]([O:19][CH3:20])=[CH:17][C:5]=3[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178486405HCID 178486405, Verbindung

Produkt 1

HCID 178486400HCID 178486400, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 3.0 g (11.3 mmol) of 8-hydroxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 20.0 mL of phosphorus oxychloride is heated under reflux for 0.5 hour, then is cooled to room temperature. Excess phosphorus oxychloride is evaporated to yield a residue, to which toluene is added and the resulting solution is reduced in vacuo. Toluene is added and evaporated twice more. The resulting residue is cooled with ice bath, neutralized with cold saturated solution of sodium bicarbonate and stirred. The solid was collected by filtration, is washed with cold water and is dried to yield 2.83 g of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid. A sample of the material is purified by silica gel chromatography, eluting with 97:3 methylene chloride/methanol to yield a yellow solid, mp.>300° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 0.5 hour
  3. customExcess phosphorus oxychloride is evaporated
  4. customto yield a residue
  5. customevaporated twice more
  6. temperatureThe resulting residue is cooled with ice bath
  7. filtrationThe solid was collected by filtration
  8. washis washed with cold water
  9. customis dried

Quellen und Nachweise

ORD-Eintrag
ord-6eae45130b0b435cb0b3c302755c6b31
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365197B2

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