5-Nitroquinoline → 5-Nitroquinolin-8-amine

HRID 866574Notes

Reaction equation

HRID 866574 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].Cl.[NH2:15]O.[OH-].[K+]>O.CO.CCO>[NH2:15][C:11]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

7

Reactant 3

HCID 118295-NitroquinolineHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 43611555-Nitroquinolin-8-amine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

To a five liter round bottom flask fitted with an air stirrer, condenser, addition funnel, thermometer and hot water bath were charged 40 g. (.23 mole) 5-nitroquinoline and 100 g. (1.44 mole) hydroxylamine hydrochloride. Then 1950 ml. of 95% EtOH was added and the solids dissolved after which 200 g. KOH in 1200 ml. MeOH was added over a 50 minute period at 54°-57° C. The mixture was allowed to stir at 55° C. for an additional hour and then dumped into 10 liters of water, allowed to cool and filtered. An orange solid was crystallized out of 95% ethanol. Such product was 8-amino-5-nitroquinoline.

Workup

  1. customTo a five liter round bottom flask fitted with an air stirrer, condenser, addition funnel
  2. dissolutionthe solids dissolved after which 200 g
  3. temperatureto cool
  4. filtrationfiltered
  5. customAn orange solid was crystallized out of 95% ethanol

Sources & evidence

ORD record
ord-eeb4f78bf4b947628e465fe261155358
Source dataset
uspto-grants-1978_07
Patent number
US04100163

Reaction notes

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