Phosphorus oxychloride → 4-Chloro-7-methoxybenzo[g]quinoline-3-carbonitrile

HRID 989342

Reaktionsgleichung

Reaktionsgleichung von HRID 989342
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:15]=[C:14]3[C:9]([C:10](=O)[C:11]([C:16]#[N:17])=[CH:12][NH:13]3)=[CH:8][C:7]=2[CH:19]=1.P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:10]1[C:9]2[C:14](=[CH:15][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][C:7]=3[CH:8]=2)[N:13]=[CH:12][C:11]=1[C:16]#[N:17]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 98136637-Methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 98351404-Chloro-7-methoxybenzo[g]quinoline-3-carbonitrileAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

A reaction mixture of 767.7 mg (3.1 mmol) of 7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile in 12 mL of phosphorus oxychloride and 5 drops of N,N-dimethylformamide (DMF) is refluxed for 2 hours. After cooling, the mixture is concentrated to dryness in vacuo to give a dark residue. The residue is partitioned between methylene chloride and ice-cooled saturated aqueous sodium carbonate solution. The organic layer is washed with ice-cooled brine and dried over sodium sulfate. The crude product is passed through a short column of silica gel, and further eluted with additional methylene chloride, followed by 95:5 methylene chloride/ethyl acetate. Removal of the solvent in vacuo yields 532.0 mg (64.7%) of 4-chloro-7-methoxybenzo[g]quinoline-3-carbonitrile as a bright yellow solid, mp 242-243° C.

Aufarbeitung

  1. temperatureis refluxed for 2 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to dryness in vacuo
  4. customto give a dark residue
  5. customThe residue is partitioned between methylene chloride and ice-
  6. temperaturecooled saturated aqueous sodium carbonate solution
  7. washThe organic layer is washed with ice-
  8. temperaturecooled brine
  9. dry with materialdried over sodium sulfate
  10. washfurther eluted with additional methylene chloride
  11. customRemoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b6974e825fe4a5bb3fe38b39da320c7
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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