Sulfuric Acid → 2-Chloro-8-nitroquinoline

HRID 513377Notes

Reaction equation

HRID 513377 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.[N+:17]([O-])([O-:19])=[O:18].[K+]>>[Cl:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 119282-ChloroquinolineHCID 24434Potassium Nitrate

Product 1

HCID 3194532-Chloro-8-nitroquinolineYield 38%

Procedure

Conc. H2SO4 was added slowly to 2-chloroquinoline (1.0 g, 6.13 mmol), followed by portionwise addition of potassium nitrate (800 mg, 7.97 mmol) at 0° C. The mixture was allowed to warm to room temperature overnight. After completion of the reaction (monitored by TLC and HPLCMS), the solution was poured slowly over ice, and the precipitate was extracted with EtOAc. The organic phase was washed with brine and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAC (17:3) as the eluent to give the title compound (450 mg, 38%).

Workup

  1. customAfter completion of the reaction (monitored by TLC and HPLCMS)
  2. additionthe solution was poured slowly over ice
  3. extractionthe precipitate was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with n-hexane/EtOAC (17:3) as the eluent

Sources & evidence

ORD record
ord-01ce627fcee14f4580f50681be706bcc
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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