m-Chloroperbenzoic acid → 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide

HRID 242435Notes

Reaction equation

HRID 242435 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[C:30]([CH3:38])[C:15]=1[C:16]([C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][N:21]=[CH:20][C:19]=1[O:28][CH3:29])=[O:17]>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[C:30]([CH3:38])[C:15]=1[C:16]([C:18]1[C:23]([C:24]([F:27])([F:25])[F:26])=[CH:22][N+:21]([O-:9])=[CH:20][C:19]=1[O:28][CH3:29])=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 121513044-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine

Product 1

HCID 121513054-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.1 g (28 mmol) of m-chloroperbenzoic acid (m-CPBA) was added at 0° C. to a chloroform 100 ml solution of 5.6 g (15 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine (Compound No. 122), followed by stirring at room temperature for 18 hours. The reaction solution was washed with a sodium hydroxide aqueous solution, and the solvent was distilled off under reduced pressure to obtain 5.8 g (yield: 99%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide (melting point 128 to 134° C.).

Workup

  1. washThe reaction solution was washed with a sodium hydroxide aqueous solution
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f1d2a354cee0439ab4ea97b32f577436
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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