8-Hydroxyquinoline → p-Toluenesulfonic acid

HRID 279769Notes

Reaction equation

HRID 279769 reaction equation
O.[C:2]1(C)[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2.[CH3:24]COCC>C(#N)C>[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[NH+:22]=[CH:21][CH:20]=[CH:19]2.[CH3:24][C:6]1[CH:5]=[CH:4][C:3]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:2][CH:7]=1

Participants

6

Reactant 3

HCID 19238-HydroxyquinolineHCID 3283Diethyl EtherHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 2

HCID 6101p-Toluenesulfonic acidHCID 5257170quinolin-1-ium-8-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The toluenesulfonic acid salt of 8-hydroxyquinoline was formed by dissolving toluenesulfonic acid monohydrate (1.9 g, 10 mmol) in acetonitrile and adding 8-hydroxyquinoline (1.45 g, 10 mmol). Removal of solvent in vacuo and addition of ether to the residual oil results in crystallization. Trituration several times with ether followed by drying in vacuo yields 8-hydroxyquinolinium, p-toluenesulfonate as a powder (3.11 g).

Workup

  1. customRemoval of solvent
  2. additionin vacuo and addition of ether to the residual oil
  3. customresults in crystallization
  4. customby drying in vacuo

Sources & evidence

ORD record
ord-3747068ec8514b65931ee3b110729e3e
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

Loading…