反応 #4194

反応方程式

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

benzene

ethanol

maleic acid

→

product

収率 55.0%

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

収率 55.0%

溶媒

ether

反応条件

後処理

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

実験手順

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.

出典