Potassium Nitrate → 5-Methyl-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 1893567Notes

Reaction equation

HRID 1893567 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 101300315-METHYL-1-INDANONE

Product 1

HCID 160947645-Methyl-6-nitro-2,3-dihydro-1H-inden-1-oneYield 55.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

This step was performed according to the method described in Journal of Medicinal Chemistry, 2006, 49, 7502-7512. 5-Methylindan-1-one (3.27 g, 22.4 mmol) was dissolved in concentrated sulfuric acid (27 ml), a solution of potassium nitrate (2.28 g, 22.6 mmol) in concentrated sulfuric acid (5 ml) was added dropwise over 10 min under ice-cooling with stirring, and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was added to ice water, and extracted with an ethyl acetate-hexane=1:1 mixed solvent. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (2.37 g, yield 55%) as a colorless solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 2 hr
  3. extractionextracted with an ethyl acetate-hexane=1:1 mixed solvent
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure
  8. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c57ad474deae41e586d4becffb904685
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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