تفاعل #72971

معادلة التفاعل

1-(aminomethyl)cyclopentanol

triethylamine

4-chloro-3-nitroquinoline

→

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

المردود 65.1%

المذيبات

dichloromethane

water

ظروف التفاعل

المعالجة

1. 1
   أخرىto stand at rt over the weekend
2. 2
   أخرىA solid formed that
3. 3
   أخرىwas isolated by filtration
4. 4
   أخرىTwo more crops of solid were isolated from the mother liquor
5. 5
   ترشيحfiltered
6. 6
   غسيلThe solid was washed with water multiple times
7. 7
   أخرىwas dried under vacuum
8. 8
   درجة الحرارةwith heat

الإجراء التجريبي

To a solution of 1-(aminomethyl)cyclopentanol (approximately 55.2 mmol, prepared as described above) in dichloromethane (280 mL) was added triethylamine (7.76 mL, 55.7 mmol) and 4-chloro-3-nitroquinoline (9.22 g, 44.3 mmol). The mixture was allowed to stand at rt over the weekend. A solid formed that was isolated by filtration. Two more crops of solid were isolated from the mother liquor. The yellow solid was stirred in water and filtered. The solid was washed with water multiple times and was dried under vacuum with heat to give 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopentanol as yellow crystals (8.29 g, 52%).

المصدر