Diethyl Sulfate → 2-(3-Ethoxyphenyl)imidazo[2,1-a]isoquinoline

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][N:11]3[CH:20]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].S(OCC)(O[CH2:27][CH3:28])(=O)=O>C(O)C>[CH2:27]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][N:11]3[CH:20]=2)[CH:5]=[CH:6][CH:7]=1)[CH3:28]

Participants

Procedure

2-(3-Hydroxyphenyl)imidazo[2,1-a]isoquinoline (2.07 g.) is added to 0.63 g. of 85 percent potassium hydroxide in 25 ml. of ethanol. To this mixture, 1.56 ml. of diethyl sulfate in 5 ml. of ethanol is added at 0° to 5° C. The mixture is maintained for 16 hours at room temperature, then is refluxed for 30 minutes. After cooling, the solution is evaporated to dryness and the residue is washed thoroughly with water. Crystallization of the solid from ethanol yields 1 g. of the title product, melting at 102°-3° C.