m-Chloroperbenzoic acid → 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide

HRID 45856

Reaction equation

HRID 45856 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:9]2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][N+:16]([O-:38])=[CH:17][CH:18]=3)[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:9]2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 671847354-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine

Product 1

HCID 671844794-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.26 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-pyridine were dissolved in 3 mL of dichloromethane and 80 mg (0.52 mmol) of m-chloroperbenzoic acid were added. The mixture was stirred at room temperature for 4 hours, diluted with the same solvent and washed with aqueous sodium hydrogenocarbonate. The organic layer was then dried over sodium sulphate and evaporated to afford, after crystallization from ethylacetate, 49 mg (47%) of the title compound.

Workup

  1. additiondiluted with the same solvent
  2. washwashed with aqueous sodium hydrogenocarbonate
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. customevaporated
  5. customto afford
  6. customafter crystallization from ethylacetate, 49 mg (47%) of the title compound

Sources & evidence

ORD record
ord-ec5d241991e2448c85173f2a5e28df02
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

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