HCID 23503591, compound → 5-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-acetyl-2,6-dichloro-4-trifluoromethylpyridine

HRID 1835414Notes

Reaction equation

HRID 1835414 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:17]([Cl:30])=[N:18][C:19]([Cl:29])=[C:20]([CH:26]([OH:28])[CH3:27])[C:21]=1[C:22]([F:25])([F:24])[F:23])[OH:15]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[C:14]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26](=[O:28])[CH3:27])[C:19]([Cl:29])=[N:18][C:17]=1[Cl:30])=[O:15]

Participants

4

Reactant 1

HCID 23503591HCID 23503591, compound

Product 1

HCID 121515445-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-acetyl-2,6-dichloro-4-trifluoromethylpyridineYield 66%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

10 g of manganese dioxide was added to a toluene (80 ml) solution of 2.3 g (5 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(2,6-dichloro-5-(1-hydroxyethyl)-4-trifluoromethyl-3-pyridyl)methanol obtained in step (a), followed by stirring under reflux by heating for 1 hour. The reaction solution was cooled to room temperature and then subjected to filtration, and toluene was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.5 g (yield 66%) of 5-(2,3,4-trimethoxy-6-methylbenzoyl)-3-acetyl-2,6-dichloro-4-trifluoromethylpyridine (compound No. 62; m.p. 109-112° C.).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 1 hour
  3. filtrationsubjected to filtration, and toluene
  4. distillationwas distilled off under reduced pressure
  5. customThe crude product thus obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-624e7fbbba0d41c18ce09617c7d31fa5
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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