8-Hydroxyquinoline → N-ethyl-8-hydroxyquinolinium ethylsulfate

HRID 918216Notes

Reaction equation

HRID 918216 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[S:12]([O-:18])([O:15][CH2:16][CH3:17])(=[O:14])=[O:13]>CC(N(C)C)=O>[CH2:16]([O:15][S:12]([O-:18])(=[O:14])=[O:13])[CH3:17].[CH2:16]([N+:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[OH:1])[CH:7]=[CH:8][CH:9]=1)[CH3:17]

Participants

4

Reactant 2

HCID 19238-Hydroxyquinoline2×HCID 3804841Ethyl sulfate anion

Product 1

HCID 21521312N-ethyl-8-hydroxyquinolinium ethylsulfateYield 78.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Into a 2-liter three-neck flask, provided with a mechanical agitator, with a reflux condenser and calcium chloride tube, and with a dropping funnel, one introduces 580 g of 8-hydroxyquinoline (i.e. 4 moles) and 800 ml of dimethylacetamide. After dissolution of the 8-hydroxyquinoline one adds, drop by drop, 616 g of freshly distilled ethyl sulfate, and then cools the reaction mixture with a bath of ice water. After heating on a steam bath for 2 hours, the solution becomes orange-yellow. One removes the dimethylformamide by means of distillation in a water-jet pump vacuum. The yellow residue is washed with anhydrous ether. The quaternary salt crystallizes after scraping. One recrystallizes the quaternary salt by dissolution in isopropanol at the rate of 1 g of quaternary salt per 1.5 ml of isopropanol. One obtains 920 g of yellow crystals which are washed thoroughly with ethyl ether.

Workup

  1. customInto a 2-liter three-neck flask, provided with a mechanical agitator, with a reflux condenser and calcium chloride tube
  2. additionadds
  3. temperatureAfter heating on a steam bath for 2 hours
  4. customOne removes the dimethylformamide
  5. distillationby means of distillation in a water-jet pump vacuum
  6. washThe yellow residue is washed with anhydrous ether
  7. customThe quaternary salt crystallizes
  8. customOne recrystallizes the quaternary salt
  9. dissolutionby dissolution in isopropanol at the rate of 1 g of quaternary salt per 1.5 ml of isopropanol

Sources & evidence

ORD record
ord-1c7d4d50e06d4d91bc5ffafeedc269a4
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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