Sodium Carbonate → 4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

HRID 612158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612158
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].C(=O)([O-])OC.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[NH4+]>CO.CC(C)=O.O>[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH:28][C:2]2[C:11]3[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=3[O:12][CH3:13])[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[C:26]([F:32])[CH:25]=1

Komponenten

10

Edukt 6

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 4585885MethylcarbonateHCID 101298981-EthoxyethanolHCID 224665354-Chloro-5,8-dimethoxyquinoline-3-carbonitrile

Produkt 1

HCID 224666204-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 0.223 g of 4-chloro-5,8-dimethoxy-3-quinolinecarbonitrile, 0.22 g of the methyl carbonate of 4-chloro-2-fluoro-5-hydroxy-aniline, and 15 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 100 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried. The solids thus obtained were dissolved in a mixture of 30 ml of methyl alcohol and 20 ml of acetone. To this mixture was added 1.5 ml of 28-30% ammonium hydroxide solution. The mixture was heated at 50° C. for 30 minutes and concentrated. The product was collected, washed with ethyl acetate, and dried to give 0.237 g of 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 240° C. (decomposed); mass spectrum (electrospray, m/e): M+H 373.9.

Aufarbeitung

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried
  6. customThe solids thus obtained
  7. concentrationconcentrated
  8. customThe product was collected
  9. washwashed with ethyl acetate
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e8831f0ef872437587e3e4a6440415bb
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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