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

HRID 1700690Notes

Reaction equation

HRID 1700690 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]=[CH: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])=[CH: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 110655617-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 23668193Sodium Nitrite

Product 1

HCID 183177547-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-1-oxideYield 71.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In benzene (4 ml) was dissolved 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (272 mg), and to the solution was added m-chloroperbenzoic acid (267 mg). The mixture was stirred at room temperature for 1 hour, and to the mixture were added ethyl acetate (70 ml), saturated sodium hydrogen carbonate solution (30 ml) and sodium nitrite (100 mg). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was washed with ethyl acetate and dried to give 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-1-oxide (205 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. washThe residue was washed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-93e551eb8b1e4275b15a69d558ab58f4
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…