반응 #4194

반응 방정식

6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

benzene

ethanol

maleic acid

→

product

수율 55.0%

1-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline maleate

수율 55.0%

용매

ether

반응 조건

후처리

1. 1
   여과The mixture was then filtered
2. 2
   기타to remove the catalyst
3. 3
   농축the filtrate was concentrated under vacuum
4. 4
   여과filtered
5. 5
   온도to cool
6. 6
   기타The supernatant was decanted from an oil, which
7. 7
   기타separated
8. 8
   농축The supernatant was concentrated

실험 절차

A Parr hydrogenation bottle was charged with 6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (16.7 g, 0.050 mole), 1% platinum-on-carbon (1 g), benzene (100 ml) and ethanol (100 ml). The mixture was shaken under an initial hydrogen pressure of 58 psi until uptake ceased. The mixture was then filtered to remove the catalyst and the filtrate was concentrated under vacuum. The residue was taken up in hot ether (150 ml), filtered, and the filtrate was treated with a hot solution of maleic acid (6.4 g, 0.055 mole) in ether (500 ml). The solution was boiled down to about 300 ml and allowed to cool. The supernatant was decanted from an oil, which separated. The supernatant was concentrated and the process was repeated several times to give 11.4 g (55%) of product. Recrystallization from ethyl acetate afforded the analytical sample, mp 113°-116° C.

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