تفاعل #42514

معادلة التفاعل

6-aminonicotinic acid

hexanal

→

3-butylimidazo[1,2-a]pyridine-6-carboxylic acid

المردود 11.9%

المذيبات

isopropyl alcohol water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   أخرىThe solids were removed by filtration
3. 3
   درجة الحرارةheated
4. 4
   درجة الحرارةat reflux 32 h
5. 5
   درجة الحرارةAfter cooling
6. 6
   أخرىthe solvents were removed under reduced pressure and MeOH
7. 7
   workup.ADDITIONwas added to the residue
8. 8
   أخرىThe resulting solid was removed by filtration
9. 9
   تركيزthe filtrate was concentrated to dryness
10. 10
    workup.ADDITIONMeOH was again added
11. 11
    أخرىthe resulting solid removed by filtration
12. 12
    أخرىAfter concentration of the filtrate, the residue was chromatographed on silica gel

الإجراء التجريبي

To hexanal (1.02 g, 10.2 mmol) in 15 mL of isopropyl alcohol-water (4:1 v/v) was added CuCl2 (1.37 g, 10.2 mmol). The mixture was heated at 80° C. for 2.5 h, then cooled. The solids were removed by filtration and the filtrate was added to 6-aminonicotinic acid (1.35 g, 10 mmol). The mixture was stirred overnight at room temperature, then heated at reflux 32 h. After cooling, the solvents were removed under reduced pressure and MeOH was added to the residue. The resulting solid was removed by filtration and the filtrate was concentrated to dryness. MeOH was again added, and the resulting solid removed by filtration. After concentration of the filtrate, the residue was chromatographed on silica gel using MeOH-dichloromethane (33/67) to give 0.26 g of 3-butylimidazo[1,2-a]pyridine-6-carboxylic acid.

المصدر