4-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

HRID 548433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548433
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[F:8]>C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Komponenten

3

Edukt 1

HCID 224666064-[(3,4-Difluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Produkt 1

HCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrileAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4.53 g (13.9 mmol) 4-[(3,4-difluorophenyl)amino]-6-nitro-quinoline-3-carbonitrile, 200 ml ethanol and 15.72 g (69.4 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1½ hours, added ice water and made basic with sodium bicarbonate. Stirred for 2 hours and extracted with chloroform. Stirred organic layer with Darco, dried with sodium sulfate and filtered. Stripped solvent and dried in vacuo, giving 3.660 g of yellow-green solid: mass spectrum (electrospray m/e): M+H=297.1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 1½ hours
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. dry with materialStirred organic layer with Darco, dried with sodium sulfate
  8. filtrationfiltered
  9. customStripped solvent and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-737e681f70a145058b766af13755d52b
Quelldatensatz
uspto-grants-2011_05
Patentnummer
USRE042376E1

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