تفاعل #73049

معادلة التفاعل

4-(aminomethyl)tetrahydro-2H-thiopyran-4-ol

triethylamine

2,4-dichloro-3-nitroquinoline

→

4-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol

المردود 59.6%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated under reduced pressure
2. 2
   أخرىsonicated for 10 minutes
3. 3
   ترشيحfiltered
4. 4
   غسيلThe isolated solid was washed extensively with water
5. 5
   أخرىdried

الإجراء التجريبي

Under a nitrogen atmosphere triethylamine (3.91 mL, 28.0 mmol) was added to a chilled (0° C.) solution of 2,4-dichloro-3-nitroquinoline (7.22 g, 26.7 mmol) in dichloromethane (100 mL). A solution of 4-(aminomethyl)tetrahydro-2H-thiopyran-4-ol (4.12 g, 28.0 mmol) in dichloromethane (30 mL) was added dropwise. The reaction mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The orange residue was combined with saturated aqueous sodium bicarbonate (50 mL) and ethyl acetate (40 mL), sonicated for 10 minutes, and then filtered. The isolated solid was washed extensively with water and then dried to provide 5.63 g of 4-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol as a yellow solid.

المصدر