8-Hydroxyquinoline → 5-Nitroso-8-quinolinol

HRID 2415118Notes

Reaction equation

HRID 2415118 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.[N:12]([O-])=[O:13].[Na+]>O.Cl>[N:12]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)=[O:13]

Participants

5

Reactant 2

HCID 19238-HydroxyquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 191035-Nitroso-8-quinolinolYield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 8-hydroxyquinoline (58 g, 0.4 mol) in distilled water, concentrated hydrochloric acid (75 ml) and ice (200 g) was added NaNO2 (30 g) in water (100 ml) at 0-4° C. during 1 hr. The reaction mixture was kept at 0° C. overnight and then filtered by washing with cold water to give 5-nitroso-8-hydroxyquinoline hydrochloide (95%).

Workup

  1. filtrationfiltered
  2. washby washing with cold water

Sources & evidence

ORD record
ord-a18efba14ef34547a818dbe55024d8cf
Source dataset
uspto-grants-2004_11
Patent number
US06818653B1

Reaction notes

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