1-Indanone → 6-Nitroindan-1-one

HRID 1696492Notes

Reaction equation

HRID 1696492 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: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 61.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 1-indanone (30 g, 0.23 mol) in conc. H2SO4 (200 mL) was added a solution of KNO3 (34 g, 0.34 mol) in conc. H2SO4 (100 mL) at 0° C. The resulting mixture was stirred for 2 h, and then poured into ice-H2O (3 L). The mixture was extracted with EtOAc (3×500 mL). The combined organic layers were washed with brine (3×500 mL), dried (Na2SO4), filtered, concentrated and purified via column chromatography to afford 6-nitro-indan-1-one (25 g, 61% yield). 1H-NMR (300 MHz, DMSO-d6): □ 8.45 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 3.20 (t, J=6.0 Hz, 2H), 2.74 (t, J=6.0 Hz, 2H).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×500 mL)
  2. washThe combined organic layers were washed with brine (3×500 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-30f140b7d951409284eeb10284255dc2
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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