Potassium Nitrate → 6-Methoxy-7-nitro-1-indanone

HRID 324624Notes

Reaction equation

HRID 324624 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:11]([N+:13]([O-:15])=[O:14])=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 117904086-Methoxy-7-nitro-1-indanoneYield 58%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 6-methoxy-1-indanone (30.0 g, 185 mmol.) in conc. sulfuric acid (130 mL) was added a solution of potassium nitrate (24.3 g, 0.24 mol.) in conc. sulfuric acid (100 mL), while maintaining the inner temperature below 0° C. The mixture was stirred for 20 minutes at the same temperature, which was then poured into ice-water, followed by extraction with ethyl acetate. The extract solution was washed with water and an aqueous solution of sodium hydrogencarbonate, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to afford the title compound (yield 21.7 g, 58%).

Workup

  1. temperaturewhile maintaining the inner temperature below 0° C
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with water
  4. dry with materialan aqueous solution of sodium hydrogencarbonate, which was then dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c4592cc2cb6c4bd6901e8a8e05f0946f
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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