反応 #4197

反応方程式

2,5-dibromonitrobenzene

1,2,3,4-tetrahydroquinoline

collidine

→

product

収率 18.0%

1-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

収率 18.0%

溶媒

1,2,3-trimethylbenzene

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   濃縮the filtrate was concentrated in vacuo (100° C.)
3. 3
   抽出the solution was extracted three times with dilute hydrochloric acid
4. 4
   乾燥once with dilute sodium hydroxide solution, three times with water, dried over anhydrous sodium sulfate
5. 5
   濃縮concentrated
6. 6
   workup.DISSOLUTIONThis residue was dissolved in 1:1 hexane
7. 7
   workup.ADDITIONcontaining 3 kg of silica gel
8. 8
   洗浄Elution with 1:1 hexane

実験手順

A stirred mixture, under nitrogen, of 2,5-dibromonitrobenzene (140.5 g, 0.50 mole), 1,2,3,4-tetrahydroquinoline (133.2 g, 1.00 mole) and symmetrical collidine (121.2 g, 1.00 mole) in 1,2,3-trimethylbenzene (500 ml) as solvent was heated at 160°-165° C. for 7 days. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated in vacuo (100° C.). The residue was taken up in dichloromethane (1.5 l) and the solution was extracted three times with dilute hydrochloric acid, once with dilute sodium hydroxide solution, three times with water, dried over anhydrous sodium sulfate and concentrated. This residue was dissolved in 1:1 hexane:toluene (250 ml) and adsorbed on a chromatography column containing 3 kg of silica gel. Elution with 1:1 hexane:toluene gave 30 g (18%) of product, as an oil. A portion of the oil was Kugelrohr distilled at an oven-temperature of 163°-165° C. (0.1 mm Hg) to provide the analytical sample.

出典