1-Indanone → 6-Nitroindan-1-one

HRID 1881256Notes

Reaction equation

HRID 1881256 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 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

1-Indanone (5.00 g, 37.8 mmol) was dissolved in sulfuric acid (40 mL), and thereto was added dropwise a solution of potassium nitrate (3.83 g, 37.8 mmol) in sulfuric acid (10 mL) under ice-cooling. The mixture was stirred for 1 hr under ice-cooling, ice was added to the reaction solution, and the mixture was stirred at room temperature overnight. The precipitated solid was collected by filtration, and purified by silica gel column chromatography (ethyl acetate/hexane=15/85→45/55) to give the title compound (4.01 g, yield 60%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionice was added to the reaction solution
  4. stirringthe mixture was stirred at room temperature overnight
  5. filtrationThe precipitated solid was collected by filtration
  6. custompurified by silica gel column chromatography (ethyl acetate/hexane=15/85→45/55)

Sources & evidence

ORD record
ord-540ce993ecd7434f9d74eacc7bec7dc0
Source dataset
uspto-grants-2012_11
Patent number
US08318784B2

Reaction notes

Loading…