Phosphorus oxychloride → 4-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile
Reaktionsgleichung
[CH3:1][O:2][C:3]1[C:4]([O:20][CH3:21])=[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:24])=O>CN(C=O)C>[Cl:24][C:10]1[C:9]2[C:14](=[CH:15][C:6]3[CH:5]=[C:4]([O:20][CH3:21])[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
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 105 °C
Versuchsvorschrift
A mixture of 356.2 mg (1.3 mmol) of 7,8-dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile in 5 mL of phosphorus oxychloride and 4 drops of DMF is heated at 100-110° C. for 4.5 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 cooled brine and dried over sodium sulfate. The organic solvent is passed through a short column of silica gel, and the column is first eluted with additional methylene chloride, then a 99:1 methylene chloride/ethyl acetate soltion. Removal of the solvent yields 187.0 mg (49.4%) of the product as a bright yellow solid, mp>265° C.
Aufarbeitung
- temperatureAfter cooling
- concentrationthe mixture is concentrated to dryness in vacuo
- customto give a dark residue
- customThe residue is partitioned between methylene chloride and ice-
- temperaturecooled saturated aqueous sodium carbonate solution
- washThe organic layer is washed with cooled brine
- dry with materialdried over sodium sulfate
- washthe column is first eluted with additional methylene chloride
- customRemoval of the solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-a7cf7a1f223a47c18c13dccddd3ef854
- Quelldatensatz
- uspto-grants-2003_10
- Patentnummer
- US06638929B2
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