O-Toluidine → 4-(2-Methylphenylamino)-3-nitroquinoline

HRID 37196

Reaktionsgleichung

Reaktionsgleichung von HRID 37196
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>C1COCC1>[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 7242O-ToluidineHCID 112758084-Chloro-3-nitroquinoline

Produkt 1

HCID 150257064-(2-Methylphenylamino)-3-nitroquinolineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Chloro-3-nitroquinoline (J. Med. Chem. 1974, 17, 245) (2.08 g, 0.01 mol) and 2-methylaniline (2.14 g, 0.02 mol) were dissolved in THF (50 ml) and the mixture stirred at reflux for 16 hours, during which time a pale yellow solid was deposited. After cooling, the solvent was evaporated and the residue dissolved in 2M HCl (80 ml). The acidic solution was extracted with CHCl3 (×3) and the chloroform solution washed with aqueous NaHCO3 and water. Drying and evaporation of the chloroform gave an orange-yellow solid which was crystallised from absolute ethanol to give the title compound (1.2 g, 43%) as orange needles, m.p. 137°-138°.

Aufarbeitung

  1. temperatureat reflux for 16 hours, during which time a pale yellow solid
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. dissolutionthe residue dissolved in 2M HCl (80 ml)
  5. extractionThe acidic solution was extracted with CHCl3 (×3)
  6. washthe chloroform solution washed with aqueous NaHCO3 and water
  7. customDrying
  8. customevaporation of the chloroform
  9. customgave an orange-yellow solid which
  10. customwas crystallised from absolute ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a21f010f71404db4b62c4eef81671f64
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420135

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