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

HRID 1835419Notes

Reaction equation

HRID 1835419 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 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) at 0° C., followed by stirring at room temperature for 18 hours. The reaction solution was washed with an aqueous sodium hydroxide 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 (m.p. 128-134° C.).

Workup

  1. customat 0° C.
  2. washThe reaction solution was washed with an aqueous sodium hydroxide solution
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-36bdf21764ab4ea3a8e80848d08acd3a
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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