Potassium Nitrate → HCID 18510818, compound

HRID 2228940Notes

Reaction equation

HRID 2228940 reaction equation
[CH:1]1([N:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:17]([O-])([O-:19])=[O:18].[K+]>S(=O)(=O)(O)O>[CH:1]1([N:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[CH:12][CH:13]=3)[C:8]2=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 110638232-Cyclohexyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 18510818HCID 18510818, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The compound (50.00 g, 0.23 mol) obtained in step (b) just above was dissolved at 0° C. in concentrated sulfuric acid (413 ml). Potassium nitrate (36.63 g, 0.36 mol) was added to the solution. The mixture was stirred overnight while gradually raising the temperature from 0° C. to room temperature. The reaction solution was poured into ice water (2000 ml), and then extracted with ethyl acetate. The extract was then washed with water, a saturated aqueous NaHCO3 solution, and saturated saline in that order, and then dried over anhydrous MgSO4. The solvent was removed by distillation under the reduced pressure. The precipitated crystals were collected by suction filtration, washed with hexane, and then dried to give 49.78 g (82%) of 2-cyclohexyl-2,3-dihydro-6-nitro-1H-isoindol-1-one as a pale yellow crystalline product.

Workup

  1. temperaturewhile gradually raising the temperature from 0° C. to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was then washed with water
  4. dry with materiala saturated aqueous NaHCO3 solution, and saturated saline in that order, and then dried over anhydrous MgSO4
  5. customThe solvent was removed by distillation under the reduced pressure
  6. filtrationThe precipitated crystals were collected by suction filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-f45b936ff9ac464f91663dca097cde33
Source dataset
uspto-grants-2002_07
Patent number
US06417362B1

Reaction notes

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