반응 #73069

반응 방정식

4-chloro-3-nitroquinoline

4-chloro-3-nitroquinoline

1-aminomethyl-1-cyclohexanol hydrochloride

4-chloro-3-nitroquinoline

3-nitroquinolin-4-ol

triethylamine

→

1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanol

수율 105.3%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도to warm to room temperature over two hours
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGthe resulting suspension was stirred for three days
4. 4
   기타The solvent was removed under reduced pressure
5. 5
   기타the residue was triturated in water for one hour
6. 6
   기타isolated by filtration
7. 7
   기타The resulting solid was triturated with hot dichloromethane
8. 8
   기타isolated by filtration from the hot mixture

실험 절차

A suspension of 1-aminomethyl-1-cyclohexanol hydrochloride (20.0 g, 121 mmol) and 4-chloro-3-nitroquinoline (24.0 g, 115 mmol) in dichloromethane (550 mL) was cooled to 0° C., and triethylamine (40 mL, 290 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to warm to room temperature over two hours. An analysis by HPLC indicated that the 4-chloro-3-nitroquinoline starting material actually contained some 3-nitroquinolin-4-ol, and additional pure 4-chloro-3-nitroquinoline (12.0 g, 57.5 mmol) was added. The reaction was stirred for four hours, and additional 1-aminomethyl-1-cyclohexanol hydrochloride (2.0 g, 12 mmol) was added, and the resulting suspension was stirred for three days. The solvent was removed under reduced pressure, and the residue was triturated in water for one hour and isolated by filtration. The resulting solid was triturated with hot dichloromethane and isolated by filtration from the hot mixture to provide 36.5 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanol as a bright yellow powder.

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