Phosphorus oxychloride → 4-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile

HRID 2213803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213803
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[CH:20][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:7]=2[CH:6]=1)[NH:14][CH:13]=[C:12]([C:17]#[N:18])[C:11]3=O.N1C2C(=CC=CC=2)C=C(C#N)C=1.P(Cl)(Cl)([Cl:38])=O>CN(C)C=O>[Cl:38][C:11]1[C:10]2[C:15](=[CH:16][C:7]3[CH:6]=[C:5]([O:4][CH2:3][CH2:2][Cl:1])[C:21]([O:22][CH3:23])=[CH:20][C:8]=3[CH:9]=2)[N:14]=[CH:13][C:12]=1[C:17]#[N:18]

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 931773-QuinolinecarbonitrileHCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 115157734-Chloro-7-methoxy-8-(2-chloroethoxy)benzo[g]quinoline-3-carbonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of 1.11 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo]quinoline-3-carbonitrile (1:1 mixture) and 5 mL of phosphorus oxychloride is added 0.15 mL of anhydrous dimethylformamide. This is stirred and heated to reflux for 20 minutes using an oil bath, followed concentration in vacuo. The dark residue is quenched with 30 mL of cold water. The solid formed is collected, washed with water and dried to give 1.02 g (87%) of 4-chloro-7-methoxy-8(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile and 4-chloro-8-methoxy-7(2-chloroethoxy)benzo[g]quinoline-3-carbonitrile (1:1 mixture) as a greenish yellow solid, m.p. 195–209° C. dec.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 20 minutes
  3. concentrationconcentration in vacuo
  4. customThe dark residue is quenched with 30 mL of cold water
  5. customThe solid formed
  6. customis collected
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5d87c812e7f841959505e28c6e32faaa
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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