反応 #4184

反応方程式

1-fluoro-2-nitrobenzene

1,2,3,4-tetrahydroquinoline

collidine

→

product

収率 22.2%

1-(2-Nitrophenyl)-1,2,3,4-tetrahydroquinoline

収率 22.2%

溶媒

1,2,3-trimethylbenzene

反応条件

後処理

1. 1
   濃縮The mixture was concentrated in vacuo
2. 2
   抽出extracted with 500 ml of 2N-hydrochloric acid
3. 3
   抽出The aqueous phase was back extracted with 250 ml of chloroform
4. 4
   洗浄The combined organic layers were washed 3 times with 2N-hydrochloric acid
5. 5
   乾燥once with 2N-sodium hydroxide solution, twice with water and dried over anhydrous sodium sulfate
6. 6
   その他The solvent was removed in vacuo
7. 7
   workup.DISSOLUTIONThe residual oil was dissolved in 300 ml of 1:1 hexane
8. 8
   workup.ADDITIONcontaining 2 kg of silica gel
9. 9
   洗浄Elution with 1:1 hexane
10. 10
    その他toluene gave fractions
11. 11
    workup.ADDITIONcontaining product
12. 12
    濃縮concentrated

実験手順

A stirred mixture, under nitrogen of 70.6 g (0.50 mole) of 1-fluoro-2-nitrobenzene, 133.2 g (1.00 mole) of 1,2,3,4-tetrahydroquinoline and 121.2 g (1.00 mole) of symmetrical collidine in 500 ml of 1,2,3-trimethylbenzene was refluxed (bp 178°) for 5 days. The mixture was concentrated in vacuo. The residue was taken up in 1000 ml of chloroform and extracted with 500 ml of 2N-hydrochloric acid. The aqueous phase was back extracted with 250 ml of chloroform. The combined organic layers were washed 3 times with 2N-hydrochloric acid, once with 2N-sodium hydroxide solution, twice with water and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The residual oil was dissolved in 300 ml of 1:1 hexane:toluene and adsorbed on a chromatography column containing 2 kg of silica gel packed in hexane. Elution with 1:1 hexane:toluene gave fractions containing product. The fractions were combined and concentrated to afford 28.2 g (22%) of product. Recrystallization from hot isopropyl ether afforded the analytical sample, mp 69°-71° C.

出典