8-Hydroxyquinoline → 8-Hydroxy-1-methylquinolinium methyl sulfate

HRID 918212Notes

Reaction equation

HRID 918212 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.[CH3:12][O:13][S:14]([O-:17])(=[O:16])=[O:15]>CC(N(C)C)=O>[CH3:12][O:13][S:14]([O-:17])(=[O:16])=[O:15].[CH3:12][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

Participants

4

Reactant 2

HCID 19238-Hydroxyquinoline2×HCID 4694097Methyl sulfate(1-)

Product 1

HCID 1979788-Hydroxy-1-methylquinolinium methyl sulfateYield 81%

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 145 g of 8-hydroxyquinoline (i.e. 1 mole) and 200 ml of dimethyl acetamide. After dissolution of the 8-hydroxyquinoline, one cools the reaction mixture with a bath of ice water and one adds, drop by drop, by means of the dropping funnel, 126 g of freshly distilled methylsulfate (i.e. 1 mole). Shortly after the completion of the addition, a light yellow compound crystallizes little by little. One continues the agitation for 2 hours after the introduction of the methylsulfate and then leaves the mixture to rest overnight in a brine bath. The quaternary salt which is formed is dried, washed with anhydrous ether and recrystallized in methanol. Weight obtained = 219 g; Melting point = 158°C; Yield = 81%.

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. additionShortly after the completion of the addition
  4. customa light yellow compound crystallizes little by little
  5. customfor 2 hours
  6. customleaves the mixture
  7. customThe quaternary salt which is formed
  8. customis dried
  9. washwashed with anhydrous ether
  10. customrecrystallized in methanol
  11. customWeight obtained = 219 g

Sources & evidence

ORD record
ord-0b27a568c9874f4d832fdf9cc69e73d7
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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