m-Chloroperbenzoic acid → 7-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one-1-oxide

HRID 1700692Notes

Reaction equation

HRID 1700692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[N:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[O:19])[CH2:9]1.ClC1C=CC=C(C(OO)=[O:28])C=1.C(=O)([O-])O.[Na+].N([O-])=O.[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N+:15]([O-:28])=[N:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[O:19])[CH2:9]1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 110439264-Methyl-7-(2-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-oneHCID 23668193Sodium Nitrite

Product 1

HCID 183175297-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one-1-oxideYield 29.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In benzene (10 ml) was dissolved 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one (1.54 g), and to the solution was added m-chloroperbenzoic acid (1.72 g). The mixture was stirred at room temperature for 1 hour, and to the mixture were added ethyl acetate (300 ml), saturated sodium hydrogen carbonate solution (300 ml) and sodium nitrite (500 mg). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydrocinnolin-5-one-1-oxide (478 mg) as pale yellow crystals.

Workup

  1. stirringThe mixture was shaken
  2. washthe separated upper layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-5977927d912c475d9c3a8c78819aa016
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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