4-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrile

HRID 548429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548429
[Cl: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]([Cl:1])[CH:3]=1

Komponenten

3

Edukt 1

HCID 110133114-[(3-Chloro-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Produkt 1

HCID 110124336-Amino-4-[(3-chloro-4-fluorophenyl)amino]-3-quinolinecarbonitrileAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5.360 g (15.6 mmol) 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-quinoline-3-carbonitrile, 250 ml ethanol, and 17.67 g (78.2 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 1½ hours and added ice water. Made basic with sodium bicarbonate. Stirred for 2 hours extracted with chloroform. Added brine to the separatory funnel to help separate layers. Stirred organic layer with Darco and dried with sodium sulfate. Filtered, stripped solvent and dried in vacuo, giving 4.460 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=312.9, 315.0.

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. customAdded brine to the separatory funnel to help separate layers
  8. dry with materialStirred organic layer with Darco and dried with sodium sulfate
  9. filtrationFiltered
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4166f67997d74a30981bd05fc67a7bf2
Quelldatensatz
uspto-grants-2011_05
Patentnummer
USRE042376E1

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