反应详情

温度

0 °C

Under a nitrogen atmosphere, a solution of 6-benzyloxy-N4-methylquinoline-3,4-diamine (7.88 g, 28.2 mmol), prepared as described in Parts A-F of Example 57, in dichloromethane (300 mL) was cooled to 0° C.; triethylamine (4.2 mL, 30.3 mmol) was added. Methoxypropionyl chloride (3.3 mL, 30.6 mmol) was added dropwise over a period of five minutes, and the reaction was stirred at ambient temperature for 90 minutes. The volatiles were removed under reduced pressure, and the residue was dissolved in ethanol (300 mL) and triethylamine (13 mL) and heated at 75° C. over two nights. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform. The resulting solution was washed with deionized water (3×200 mL) and concentrated under reduced pressure. Small volumes of hexanes and dichloromethane were added, and a white precipitate formed, which was isolated by filtration and washed with hexanes to provide 3.76 g of 8-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline as a white solid.

1. customThe volatiles were removed under reduced pressure
2. dissolutionthe residue was dissolved in ethanol (300 mL)
3. temperaturetriethylamine (13 mL) and heated at 75° C. over two nights
4. customThe volatiles were removed under reduced pressure
5. dissolutionthe residue was dissolved in chloroform
6. washThe resulting solution was washed with deionized water (3×200 mL)
7. concentrationconcentrated under reduced pressure
8. additionSmall volumes of hexanes and dichloromethane were added
9. customa white precipitate formed
10. customwhich was isolated by filtration
11. washwashed with hexanes