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

HRID 616717Notes

Reaction equation

HRID 616717 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

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14797Potassium HydroxideHCID 13156070HCID 13156070, compound

Product 1

HCID 131560722-(3-Ethoxyphenyl)imidazo[2,1-a]isoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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.

Workup

  1. temperatureis refluxed for 30 minutes
  2. temperatureAfter cooling
  3. customthe solution is evaporated to dryness
  4. washthe residue is washed thoroughly with water
  5. customCrystallization of the solid from ethanol
  6. customyields 1 g

Sources & evidence

ORD record
ord-5e3c9b1d38074db185496ccb0e33a8a9
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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