2-Chloroquinoline → 2-Chloro-5-nitroquinoline

HRID 2182680Notes

Reaction equation

HRID 2182680 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1

Participants

4

Reactant 2

HCID 119282-ChloroquinolineHCID 24434Potassium Nitrate

Product 1

HCID 3192512-Chloro-5-nitroquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

10.0 g (61.1 mmol) of 2-chloroquinoline is dissolved in 34 ml of concentrated sulfuric acid. At 0° C., 8.4 g (76.4 mmol) of potassium nitrate is added in portions. After 20 hours at room temperature, the reaction mixture is poured onto ice water, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium bicarbonate solution and dried on sodium sulfate. After the solvent is removed in a vacuum and after chromatography on silica gel with hexane-ethyl acetate (10-100%), 5.06 g (40% of theory) of the product is obtained.

Workup

  1. additionthe reaction mixture is poured onto ice water
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium bicarbonate solution
  4. customdried on sodium sulfate
  5. customAfter the solvent is removed in a vacuum
  6. customafter chromatography on silica gel with hexane-ethyl acetate (10-100%), 5.06 g (40% of theory) of the product is obtained

Sources & evidence

ORD record
ord-cf619f9fc4e04a43881740cb6bfcf838
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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