Reaction #94294

Reaction equation

2-(4-methoxyphenyl)imidazo[1,2-a]pyridine

methyl iodide

methyl iodide

→

1-methyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridinium iodide

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturerefluxed for 3 hrs
2. 2
   Temperaturereflux
3. 3
   OtherThe solids which precipitate
4. 4
   Temperatureon cooling
5. 5
   Filtrationare filtered
6. 6
   workup.DISSOLUTIONpartially dissolved
7. 7
   Filtrationfiltered
8. 8
   TemperatureThe isopropanol filtrate is cooled
9. 9
   workup.ADDITIONtreated with diethyl ether
10. 10
    FiltrationThe crystallized product is filtered
11. 11
    Otherdried
12. 12
    Otherto give 1.03 g

Procedure

To 2.23 g. of 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine in 50 ml. of acetonitrile is added 2.84 g. of methyl iodide, and the resulting reaction mixture refluxed for 3 hrs. Additional methyl iodide (2 ml.) is added and reflux continued for one hour. The solids which precipitate on cooling are filtered and partially dissolved in boiling isopropanol and filtered. The isopropanol filtrate is cooled and treated with diethyl ether. The crystallized product is filtered and dried to give 1.03 g., m.p. 194-196° C.

Source