Nitric Acid → HCID 14576878, compound

HRID 1904631Notes

Reaction equation

HRID 1904631 reaction equation
[C:1]1([N:7]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH2:11][CH2:10][CH2:9][C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:22]([O-])([OH:24])=[O:23].[OH-].[Na+]>C(OC(=O)C)(=O)C>[N+:22]([C:4]1[CH:3]=[CH:2][C:1]([N:7]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH2:11][CH2:10][CH2:9][C:8]2=[O:21])=[CH:6][CH:5]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 14576877HCID 14576877, compound

Product 1

HCID 14576878HCID 14576878, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 1.0 g of 1-phenyl-6-(3,4-dichlorophenyl)-2-piperidone in 0.5 ml of acetic anhydride was added 1 ml of fuming nitric acid at 0° to 10° C., and the mixture was stirred for 3 hours. The mixture was made alkaline under cooling with an aqueous 10% sodium hydroxide solution and extracted with toluene. After washing with water and drying, the solvent was evaporated. The residue was purified by silica gel column chromatography (solvent; acetone:n-hexane=1:1) to give 0.35 g of 1-(4-nitrophenyl)-6-(3,4-dichlorophenyl)-2-piperidone as colorless foam.

Workup

  1. extractionextracted with toluene
  2. washAfter washing with water
  3. customdrying
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (solvent; acetone:n-hexane=1:1)

Sources & evidence

ORD record
ord-5596dd14e68244b883b725db7341062f
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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