反応 #9512

反応方程式

thionyl chloride

thionyl chloride

4-(7-bromo-3-nitroquinolin-4-ylamino)butan-1-ol

sodium bicarbonate

→

(7-bromo-3-nitroquinolin-4-yl)-(4-chlorobutyl)amine

収率 37.9%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度to warm to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   その他The aqueous layer was separated
4. 4
   抽出extracted with dichloromethane (3×100 mL)
5. 5
   乾燥The combined organic fractions were dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他to yield an orange semi-solid
9. 9
   その他the crude product was purified by column chromatography on silica gel (
10. 10
    洗浄eluting with dichloromethane

実験手順

A suspension of 4-(7-bromo-3-nitroquinolin-4-ylamino)butan-1-ol (20.75 g, 61.0 mmol) in dichloromethane (220 mL) was cooled to 0° C.; thionyl chloride (4.90 mL, 67.1 mmol) was added dropwise over a period of ten minutes. The reaction was stirred at 0° C. for five minutes, allowed to warm to ambient temperature, and stirred overnight. Aqueous sodium bicarbonate (500 mL of 50%) was slowly added. The aqueous layer was separated and extracted with dichloromethane (3×100 mL). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield an orange semi-solid. An analysis by LCMS indicated the presence of starting material, and the semi-solid was dissolved in dichloromethane (150 mL) and treated with thionyl chloride (3.0 mL) as described above. Following the work-up procedure, the crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 100:0 to 95:5) to provide 8.3 g of (7-bromo-3-nitroquinolin-4-yl)-(4-chlorobutyl)amine as a yellow solid.

出典