反応 #65474

反応方程式

4-Chloro-3-nitroquinoline

2-methylaniline

→

title compound

収率 43.0%

4 - (2 -Methylphenylamino)-3 -nitroquinoline

収率 43.0%

溶媒

THF

反応条件

後処理

1. 1
   温度at reflux for 16 hours, during which time a pale yellow solid
2. 2
   温度After cooling
3. 3
   その他the solvent was evaporated
4. 4
   workup.DISSOLUTIONthe residue dissolved in 2M HCl (80 ml)
5. 5
   抽出The acidic solution was extracted with CHCl3 (×3)
6. 6
   洗浄the chloroform solution washed with aqueous NaHCO3 and water
7. 7
   その他Drying
8. 8
   その他evaporation of the chloroform
9. 9
   その他gave an orange-yellow solid which
10. 10
    その他was crystallised from absolute ethanol

実験手順

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°.

出典