1-Indanone → 6-Nitroindan-1-one

HRID 324984Notes

Reaction equation

HRID 324984 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[N+:11]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][C:1]2=[O:10])=[CH:5][CH:6]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 24434Potassium Nitrate

Product 1

HCID 905626-Nitroindan-1-oneYield 129.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-indanone (25.0 g, 189 mmol) in concentrated sulfuric acid (84 mL) at 0° C. was added a solution of potassium nitrate (8.33 g, 82.4 mmol) in sulfuric acid (40 mL) at a rate sufficient to maintain an internal temperature below 15° C. After the addition was complete, the reaction was allowed to stir at 0° C. for 1 hour. The reaction mixture was then poured into crushed ice and stirred vigorously for 30 minutes. The suspension was then filtered, air dried, and purified by liquid chromatography (50 ethyl acetate/toluene) to provide 18.90 g of the title compound. (56%).

Workup

  1. temperatureto maintain an internal temperature below 15° C
  2. additionAfter the addition
  3. additionThe reaction mixture was then poured
  4. custominto crushed ice
  5. stirringstirred vigorously for 30 minutes
  6. filtrationThe suspension was then filtered
  7. customair dried
  8. custompurified by liquid chromatography (50 ethyl acetate/toluene)

Sources & evidence

ORD record
ord-ed7ce624495248b9883aa0ef01b11b0c
Source dataset
uspto-grants-2001_04
Patent number
US06221876B1

Reaction notes

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