m-Chloroperbenzoic acid → HCID 70079466, compound

HRID 1953417Notes

Reaction equation

HRID 1953417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([N:17]3[C:22](=[O:23])[C:21]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[N:20][C:19]4[CH:31]=[CH:32][CH:33]=[N:34][C:18]3=4)[CH:14]=[CH:15][CH:16]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([N:17]3[C:22](=[O:23])[C:21]([CH2:24][C:25]4[CH:26]=[N+:27]([O-:43])[CH:28]=[CH:29][CH:30]=4)=[N:20][C:19]4[CH:31]=[CH:32][CH:33]=[N:34][C:18]3=4)[CH:14]=[CH:15][CH:16]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22724401HCID 22724401, compound

Product 1

HCID 70079466HCID 70079466, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-[(E)-2-(3,5-dichlorophenyl)vinyl]phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (255 mg) in dichloromethane (10 ml) was added m-chloroperbenzoic acid (181 mg). The mixture was stirred at room temperature for 1 hour, then poured into aqueous sodium bicarbonate and extracted with chloroform. The organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was washed with diisopropyl ether to give 4-[3-[(E)-2-(3,5-dichlorophenyl) vinyl]phenyl]-2-[(1-oxido-3-pyridyl)methyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (167 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic solution was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe resultant solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-4a329f51e8ed4709bffe376182aa9295
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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