1-Indanone → 6-Nitroindan-1-one

HRID 1725904Notes

Reaction equation

HRID 1725904 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+].[N+](C1C=CC=C2C=1CCC2=O)([O-])=O>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

5

Reactant 3

HCID 67351-IndanoneHCID 24434Potassium NitrateHCID 905634-Nitroindan-1-one

Product 1

HCID 905626-Nitroindan-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of concentrated H2SO4 at 0° C. was treated with 1-indanone (6.00 g, 45.4 mmol) then treated dropwise with KNO3 (5.00 g, 49.94 mmol) in concentrated H2SO4 while maintaining the internal temperature at no more than 15° C. The reaction was stirred for 1 hour after the addition was complete, then poured onto ice. The resulting solids were collected by filtration, washed with water, and dried under vacuum to give a 4:1 mixture of 6-nitro- and 4-nitro-1-indanone (5.04 g, 63%). MS (ESI(+) m/e 178 (M+H)+, 195 (M+NH4)+; MS (ESI(−)) m/e 176 (M−H)−; 1H NMR (300 MHz, DMSO-d6, 6-nitro-1-indanone) δ 8.49 (dd, 1H), 8.29 (d, 1H), 7.87 (d, 1H), 3.25 (m, 2H), 2.78 (m, 2H); 1H NMR (300 MHz, DMSO-d6), 4-nitro-1-indanone) δ 8.51 (dd, 1H), 8.07 (dd, 1H), 7.74 (t, 1H), 3.53 (m, 2H), 2.76 (m, 2H).

Workup

  1. temperaturewhile maintaining the internal temperature at no more than 15° C
  2. additionafter the addition
  3. additionpoured onto ice
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with water
  6. customdried under vacuum
  7. customto give

Sources & evidence

ORD record
ord-eb2734fd6f974ef08948607e52a50df6
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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