반응 #65474

반응 방정식

4-Chloro-3-nitroquinoline

2-methylaniline

→

title compound

수율 43.0%

4 - (2 -Methylphenylamino)-3 -nitroquinoline

수율 43.0%

용매

THF

반응 조건

후처리

1. 1
   온도at reflux for 16 hours, during which time a pale yellow solid
2. 2
   온도After cooling
3. 3
   기타the solvent was evaporated
4. 4
   workup.DISSOLUTIONthe residue dissolved in 2M HCl (80 ml)
5. 5
   추출The acidic solution was extracted with CHCl3 (×3)
6. 6
   세척the chloroform solution washed with aqueous NaHCO3 and water
7. 7
   기타Drying
8. 8
   기타evaporation of the chloroform
9. 9
   기타gave an orange-yellow solid which
10. 10
    기타was crystallised from absolute ethanol

실험 절차

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°.

출처