反应详情

A mixture of 1.58 g of 6-chloronicotinic acid and 1.62 g of 1,1'-carbonyldiimidazole in 30 ml of tetrahydrofuran was stirred at room temperature for 3 hours. Then 1.95 g of 1H-imidazole-1-octanamine was added and the mixture was stirred at room temperature for 16 hours. The mixture was heated at reflux for 5 hours, 10 ml of water was added and heating was continued for one hour longer. The mixture was concentrated to remove tetrahydrofuran. Then 5 ml of 1N sodium hydroxide and dichloromethane was added. The mixture was shaken and the organic layer was separated, washed twice with water, dried over magnesium sulfate and filtered. The filtrate was concentrated and gave an oil. The oil was treated with diethyl ether to crystallize the desired compound as white crystals, mp 79°-81° C.

1. stirringthe mixture was stirred at room temperature for 16 hours
2. temperatureThe mixture was heated
3. temperatureat reflux for 5 hours
4. temperatureheating
5. waitwas continued for one hour
6. concentrationThe mixture was concentrated
7. customto remove tetrahydrofuran
8. additionThen 5 ml of 1N sodium hydroxide and dichloromethane was added
9. stirringThe mixture was shaken
10. customthe organic layer was separated
11. washwashed twice with water
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationThe filtrate was concentrated
15. customgave an oil
16. customto crystallize the desired compound as white crystals, mp 79°-81° C.