m-Chloroperbenzoic acid → 2-[(Z)-C-(4-chloro-5-fluoro-2-hydroxyphenyl)-N-[(2-methylpropan-2-yl)oxy]carbonimidoyl]-1-oxidopyridin-1-ium-3-ol

HRID 862094Notes

Reaction equation

HRID 862094 reaction equation
[C:1]([O:5]/[N:6]=[C:7](\[C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1)/[C:8]1[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5]/[N:6]=[C:7](\[C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N+:18]=1[O-:32])/[C:8]1[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=1[OH:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 136463740HCID 136463740, compound

Product 1

HCID 1355154542-[(Z)-C-(4-chloro-5-fluoro-2-hydroxyphenyl)-N-[(2-methylpropan-2-yl)oxy]carbonimidoyl]-1-oxidopyridin-1-ium-3-olYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (Z)-2-(4-chloro-5-fluoro-2-hydroxybenzoyl)-3-hydroxypyridine O-t-butyloxime (0.82 g) in chloroform (30 ml) was added 70% m-chloroperbenzoic acid (1.01 g) at 0° C. The mixture was warmed up to room temperature and stirred for 5 hours. To the reaction mixture was added an aqueous solution of sodium hydrogensulfite to quench the reaction. The reaction mixture was subjected to extraction with chloroform. The organic layer was dried (anhydrous magnesium sulfate). The solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography to give (Z)-2-(4-chloro-5-fluoro-2-hydroxybenzoyl)-3-hydroxypyridine N-oxide O-t-butyloxime (0.79 g) (Compound 56).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction mixture was subjected to extraction with chloroform
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-e74202eb8a91483f929a82f48aab6058
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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