3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 396179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396179
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Cl:19][C:20]1[CH:21]=[C:22]([NH2:27])[CH:23]=[CH:24][C:25]=1[F:26]>CC(O)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:23]=[CH:24][C:25]=1[F:26]

Komponenten

4

Edukt 2

HCID 97083-Chloro-4-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Produkt 1

HCID 108940424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrileAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

An amount of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile (7.1 g, 26.9 mmol), and 3-chloro-4-fluoro-phenylamine (3.9 g, 26.8 mmol), were stirred in 2-propanol (70 mL), and heated at reflux for 2 hours. The mixture was cooled to room temperature and stirred for an additional 20 hours. The reaction mixture was evaporated to dryness, stirred with ethyl acetate and saturated sodium bicarbonate solution. After separation of the layers, the organic layer was washed with saturated brine solution and dried on magnesium sulfate, to give a dark green powder (9.9 g, 99%), which was used without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture was evaporated to dryness
  4. stirringstirred with ethyl acetate and saturated sodium bicarbonate solution
  5. customAfter separation of the layers
  6. washthe organic layer was washed with saturated brine solution
  7. customdried on magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-02b0de6ba631466580d08addf87b88f4
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608048B2

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