8-Methylquinoline → 8-Methyl-5-nitroquinoline

HRID 751060

Reaction equation

HRID 751060 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N+:12]([O-])([O-:14])=[O:13].[K+]>OS(O)(=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 119108-MethylquinolineHCID 24434Potassium Nitrate

Product 1

HCID 2463008-Methyl-5-nitroquinolineYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of commercially available 8-methylquinoline (5.0 g, 34 mmol) in concentrated H2SO4 (19 mL) at 0° C. was added portionwise KNO3 (4.29 g, 42.4 mmol). After the addition, the reaction was stirred at rt for 17 h, then poured into ice/water and extracted with EtOAc (3×100 mL). The aqueous layer was basified to pH=9 with solid Na2CO3 and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) to yield the title compound (5.98 g, 94%) as a light yellow solid. LC/MS m/z 189 [M+H]+.

Workup

  1. additionAfter the addition
  2. extractionextracted with EtOAc (3×100 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (silica gel)

Sources & evidence

ORD record
ord-7ca05091e8f4426e998fd20961bdae50
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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