Phosphorus oxychloride → 8-(Benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 2213841

Reaktionsgleichung

Reaktionsgleichung von HRID 2213841
[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[NH:18][CH:17]=[C:16]([C:21]#[N:22])[C:15]3=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:30])=O>>[CH2:1]([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[N:18]=[CH:17][C:16]([C:21]#[N:22])=[C:15]3[Cl:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 117726788-Benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 219564648-(Benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrileAusbeute 97,9 %

Versuchsvorschrift

A mixture of 8-benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (11.4 g, 31.9 mmol) and phosphorus oxychloride (147 g, 959 mmol) is heated under reflux for one hour. After cooling to room temperature, the reaction mixture is evaporated under vacuum to remove the volatiles. The residue is carefully slurried in cold saturated aqueous sodium bicarbonate solution (500 mL). The solids are collected by filtration, washed thoroughly with saturated aqueous sodium bicarbonate solution and water and dried to give 11.7 grams of crude 8-(benzyloxy)-4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile as a light orange solid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for one hour
  3. customthe reaction mixture is evaporated under vacuum
  4. customto remove the volatiles
  5. filtrationThe solids are collected by filtration
  6. washwashed thoroughly with saturated aqueous sodium bicarbonate solution and water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-18cdf3b7421b4f31a4a547e3d58e4933
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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