反应 #4136

反应方程式

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

benzene

ethanol

maleic acid

→

product

收率 55.0%

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

收率 55.0%

溶剂

ether

反应条件

后处理

1. 1
   过滤The mixture was then filtered
2. 2
   其他to remove the catalyst
3. 3
   浓缩the filtrate was concentrated under vacuum
4. 4
   过滤filtered
5. 5
   温度to cool
6. 6
   其他The supernatant was decanted from an oil, which
7. 7
   其他separated
8. 8
   浓缩The supernatant was concentrated

实验过程

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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