m-Chloroperbenzoic acid → 5-(2-Carboxy-4-cyclopropylphenylamino)-3-methyl-2-phenylpyridine 1-oxide

HRID 42055Notes

Reaction equation

HRID 42055 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([NH:13][C:14]3[CH:15]=[N:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:18]([CH3:20])[CH:19]=3)=[C:8]([CH:12]=2)[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>ClCCl>[C:9]([C:8]1[CH:12]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[CH:6][C:7]=1[NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N+:16]([O-:35])[CH:15]=1)([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 569684665-Cyclopropyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid

Product 1

HCID 251861735-(2-Carboxy-4-cyclopropylphenylamino)-3-methyl-2-phenylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-cyclopropyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid (0.29 mmol, 0.1 g) in 4 ml of dichloromethane was added mCPBA in portions, at 0° and under argon atmosphere. After the addition the mixture was stirred overnight at room temperature. The solvent was evaporated and the solid residue was triturated with a water/ethyl acetate mixture. The solid was filtered off affording 0.035 g (33% of yield) of the expected product.

Workup

  1. customat 0°
  2. additionAfter the addition the mixture
  3. customThe solvent was evaporated
  4. customthe solid residue was triturated with a water/ethyl acetate mixture
  5. filtrationThe solid was filtered off
  6. customaffording

Sources & evidence

ORD record
ord-11cd2034742a420291318ff8eca7a3e6
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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