反应 #4139

反应方程式

2,5-dibromonitrobenzene

1,2,3,4-tetrahydroquinoline

collidine

→

product

收率 18.0%

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

收率 18.0%

溶剂

1,2,3-trimethylbenzene

反应条件

后处理

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

实验过程

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.

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