Реакция #73049

Уравнение реакции

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

Выход 59.6%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated under reduced pressure
2. 2
   Другоеsonicated for 10 minutes
3. 3
   Фильтрацияfiltered
4. 4
   ПромывкаThe isolated solid was washed extensively with water
5. 5
   Другоеdried

Методика

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.

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