Hydrochloric Acid → 5-Aminoquinolin-8-ol--hydrogen chloride (1/2)

HRID 2415119Notes

Reaction equation

HRID 2415119 reaction equation
[Cl-:1].[N:2]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)=O.[OH-].[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>O>[ClH:1].[ClH:1].[NH2:2][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 22640702HCID 22640702, compound

Product 1

HCID 162119475-Aminoquinolin-8-ol--hydrogen chloride (1/2)Yield 152.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

5-nitroso-8-hydroxyquinoline chloride (40 g) was added to a mixture of water (160 ml) and 5N-NaOH (260 ml) and heated to 40° C. Na2S2O4 (95 g) was added to the reaction mixture wraith increasing temperature to 75-80° C. The reaction mixture was cooled to 50° C. and 12N-HCl (250 ml) was added to it. Then the reaction mixture was cooled to 0° C. and filtered to give 5-amino-8-hydroxyquinoline dihydrochloride (34 g, 69%).

Workup

  1. temperaturewraith increasing temperature to 75-80° C
  2. temperatureThe reaction mixture was cooled to 50° C.
  3. temperatureThen the reaction mixture was cooled to 0° C.
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7af0890c9b1a4d47a58c4fa9964ce53c
Source dataset
uspto-grants-2004_11
Patent number
US06818653B1

Reaction notes

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