1-Indanone → 6-Nitroindan-1-one

HRID 1802670Notes

Reaction equation

HRID 1802670 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-a5d95964e66a4ff4bdc471bf7599939c
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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