1-Indanone → 4-Nitroindan-1-one

HRID 241796

Reaction equation

HRID 241796 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+]>OS(O)(=O)=O>[N+:11]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH2:3][CH2:2][C:1]2=[O:10])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 24434Potassium Nitrate

Product 1

HCID 905634-Nitroindan-1-oneYield 18%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a 0° C. solution of indanone (1.1 mL, 9.16 mmol, 1.0 equiv) in concentrated H2SO4 (9 mL) was added KNO3 (926 mg, 9.16 mmol, 1.0 equiv) as a solid in several portions over 5 min. After stirring for 1 h, the reaction mixture was poured onto ice. The aqueous suspension was extracted with EtOAC (3×30 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (20%-50% EtOAc/Hexanes) provided the desired compound as a yellow solid (288 mg, 18%).

Workup

  1. additionthe reaction mixture was poured onto ice
  2. extractionThe aqueous suspension was extracted with EtOAC (3×30 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (20%-50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-871bc7f085234c478a2c51f204a17fe0
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Linked notes

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