4-Chloro-6-nitroquinoline-3-carbonitrile → 4-[(3-Chloro-4thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 612096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612096
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:21]>C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrileHCID 234380833-Chloro-4-(phenylsulfanyl)aniline

Produkt 1

HCID 1317214944-[(3-Chloro-4thiophenoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrileAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, and 6.07 g (25.6 mmol) 3-chloro-4-thiophenoxyaniline was heated to reflux under N2. Removed heat at about 8 hours, made basic with saturated sodium bicarbonate, stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected solids. Washed with water and dried in vacuo. Dissolved nearly completely in 400 ml ethyl acetate, stirred with Darco and filtered. Stripped solvent and boiled in hexane to remove last of the excess aniline. Dried in vacuo, giving 6.90 g of red solid: mass spectrum (electrospray m/e): M+H=433.1, 435.1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at about 8 hours
  5. customazeotroped with ethanol
  6. customcollected solids
  7. washWashed with water
  8. customdried in vacuo
  9. dissolutionDissolved nearly completely in 400 ml ethyl acetate
  10. filtrationfiltered
  11. customto remove last of the excess aniline
  12. customDried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b946540427f44d1ead18f87f6b08087b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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