m-Chloroperbenzoic acid → 3-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamide 1-oxide

HRID 78765Notes

Reaction equation

HRID 78765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:20]=[N:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][O:14][CH2:15][CH3:16])=[O:12])=[C:4]([CH3:21])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:20]=[N+:19]([O-:30])[CH:18]=[CH:17][C:10]=2[C:11]([NH:13][O:14][CH2:15][CH3:16])=[O:12])=[C:4]([CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 576496563-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamide

Product 1

HCID 576496153-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamide 1-oxideYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(4-Bromo-2-methylphenyl)amino]-N-ethoxyisonicotinamide 3b (80.0 mg, 0.228 mmol) was dissolved in 4 ml dry DCM and 3-chloroperbenzoic acid (73% pure, 60 mg) was added at ambient temperature. After 2 h the solvent was removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 37 mg (101 μmol; 44% yield) of pure desired product.

Workup

  1. customAfter 2 h the solvent was removed in vacuo
  2. customthe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-96a19afd25274aedadbdfda36359be6b
Source dataset
uspto-grants-2014_09
Patent number
US08841459B2

Reaction notes

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