반응 #63418

반응 방정식

2,5-dibromonitrobenzene

1,2,3,4-tetrahydroquinoline

collidine

→

product

수율 18.0%

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

수율 18.0%

용매

1,2,3-trimethylbenzene

반응 조건

후처리

1. 1
   여과filtered
2. 2
   농축the filtrate was concentrated in vacuo (100° C.)
3. 3
   추출the solution was extracted three times with dilute hydrochloric acid
4. 4
   건조once with dilute sodium hydroxide solution, three times with water, dried over anhydrous sodium sulfate
5. 5
   농축concentrated
6. 6
   workup.DISSOLUTIONThis residue was dissolved in 1:1 hexane
7. 7
   workup.ADDITIONcontaining 3 kg of silica gel
8. 8
   세척Elution with 1:1 hexane

실험 절차

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°-65° 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°-65° C. (0.1 mm Hg) to provide the analytical sample.

출처