Nitric Acid → 4-Chloro-8-nitroquinoline

HRID 554479Notes

Reaction equation

HRID 554479 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18].[OH-].[NH4+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:17]([O-:19])=[O:18])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 691404-Chloroquinoline

Product 1

HCID 6104404-Chloro-8-nitroquinolineYield 55.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloroquinoline (5 g, 31 mmol) was dissolved in sulfuric acid (23 mL, 0.42 mol), to which nitric acid (4.5 mL, 0.11 mol) was slowly added dropwise, which was then stirred at room temperature for four hours. When the reaction was completed, the resultant was cooled to 0° C., and neutralized with 1M ammonium hydroxide. The generated solid was dissolved in ethyl acetate, dried with anhydrous sodium sulfate, and then filtered. The solvent was removed by vacuum distillation, and the residue was purified by a column chromatography (ethyl acetate/n-hexane=⅓) to obtain 3.55 g of the desired compound as a white solid (yield 55.7%).

Workup

  1. additionwas slowly added dropwise
  2. temperaturethe resultant was cooled to 0° C.
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by vacuum distillation
  6. customthe residue was purified by a column chromatography (ethyl acetate/n-hexane=⅓)

Sources & evidence

ORD record
ord-cd4922cae4384d539190db6a3959f622
Source dataset
uspto-grants-2011_11
Patent number
US08049014B2

Reaction notes

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