Toluene → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine

HRID 1835425Notes

Reaction equation

HRID 1835425 reaction equation
CN(C)P(=O)(N(C)C)N(C)C.[CH3:12][O-:13].[Na+].C1(C)C=CC=CC=1.[CH3:22][O:23][C:24]1[C:39]([O:40][CH3:41])=[C:38]([O:42][CH3:43])[CH:37]=[C:36]([CH3:44])[C:25]=1[C:26]([C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[CH:30][C:29]=1Cl)=[O:27]>O>[CH3:22][O:23][C:24]1[C:39]([O:40][CH3:41])=[C:38]([O:42][CH3:43])[CH:37]=[C:36]([CH3:44])[C:25]=1[C:26]([C:28]1[C:29]([O:13][CH3:12])=[CH:30][N:31]=[CH:32][C:33]=1[Cl:34])=[O:27]

Participants

6

Reactant 4

HCID 1140TolueneHCID 12679HexamethylphosphoramideHCID 10942334Sodium MethoxideHCID 23503602HCID 23503602, compound

Product 1

HCID 235035934-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridineYield 690.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (2.8 mmol) of hexamethylphosphoric triamide and 1.1 g (2.1 mmol) of sodium methoxide were added to a toluene (60 ml) solution of 5.0 g (1.4 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3,5-dichloropyridine (compound No. 191), followed by stirring under reflux by heating for 5 hours. After the mixture was cooled, 50 ml of water was added to the mixture to terminate the reaction, and ethyl acetate was added thereto for extraction. The organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 3.4 g (yield 69%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine (compound No. 244; pale yellow oily substance).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 5 hours
  3. temperatureAfter the mixture was cooled
  4. customto terminate
  5. customthe reaction, and ethyl acetate
  6. additionwas added
  7. extractionfor extraction
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationsubjected to filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe crude product thus obtained
  12. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4e419e4e46494ffa9f282ac9769be4de
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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