m-Chloroperbenzoic acid → 3-nitro-2-[3-[(E)-2-(1-oxido-3-pyridyl)vinyl]phenylamino]pyridine

HRID 1953412Notes

Reaction equation

HRID 1953412 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[N+:21]([O-:33])[CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 227244742-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridine

Product 1

HCID 232981173-nitro-2-[3-[(E)-2-(1-oxido-3-pyridyl)vinyl]phenylamino]pyridineYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-nitro-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridine (2.22 g) in dichloromethane (70 ml) was added m-chloroperbenzoic acid (1.81 g). 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 residue was chromatographed on silica gel column (8% methanol in chloroform) to give 3-nitro-2-[3-[(E)-2-(1-oxido-3-pyridyl)vinyl]phenylamino]pyridine (1.51 g).

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. customThe residue was chromatographed on silica gel column (8% methanol in chloroform)

Sources & evidence

ORD record
ord-814ea7312619453daad8858555c3d16c
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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