反应 #4100

反应方程式

5-chloro-1-(4-chloro-2-nitrophenyl)indoline

benzene

→

1-(2-amino-4-chlorophenyl)-5-chloroindoline hydrochloride ethanolate

溶剂

ethanol

反应条件

后处理

1. 1
   其他The catalyst was then removed by filtration
2. 2
   浓缩the filtrate was concentrated in vacuo to an oil
3. 3
   workup.DISSOLUTIONThis was dissolved in 30 ml of ethanol
4. 4
   workup.ADDITION30 ml of ether saturated with hydrogen chloride was added
5. 5
   workup.ADDITIONAn additional 500 ml of plain ether was added
6. 6
   workup.STIRRINGthe mixture was stirred at 0° C.
7. 7
   其他precipitation
8. 8
   其他The hydrochloride salt was collected
9. 9
   其他dried
10. 10
    其他Recrystallization from ethanol (charcoal)

实验过程

A Parr bottle, charged with 12.4 g (0.040 mole) of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline of Example 8a, 100 ml of benzene, 100 ml of absolute ethanol and 0.5 g of 1% Pt/C was shaken under an initial hydrogen pressure of 57 psig until uptake ceased. The catalyst was then removed by filtration and the filtrate was concentrated in vacuo to an oil weighing 11.2 g (100%). This was dissolved in 30 ml of ethanol and then 30 ml of ether saturated with hydrogen chloride was added. An additional 500 ml of plain ether was added, and the mixture was stirred at 0° C., to maximize precipitation. The hydrochloride salt was collected, dried, and found to weigh 9.2 g (73%), m.p. 174°-178° C. Recrystallization from ethanol (charcoal) afforded 1-(2-amino-4-chlorophenyl)-5-chloroindoline hydrochloride ethanolate in 58% overall yield, m.p. 177°-180° C.

来源