Dimethylformamide → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-2,3-dichloro-5-methoxypyridine

HRID 1835427Notes

Reaction equation

HRID 1835427 reaction equation
CN(C)C=O.P(Cl)(Cl)([Cl:8])=O.[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:14]=1[C:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][N+:20]([O-])=[CH:19][C:18]=1[Cl:26])=[O:16]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[C:27]([CH3:35])[C:14]=1[C:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][N:20]=[C:19]([Cl:8])[C:18]=1[Cl:26])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 235035884-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide

Product 1

HCID 235035954-(2,3,4-Trimethoxy-6-methylbenzoyl)-2,3-dichloro-5-methoxypyridineYield 739.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 ml of dimethylformamide was added to 2.5 ml of toluene, the mixture was cooled with ice, and 1.3 ml (1.4 mmol) of phosphorus oxychloride was dropwise added thereto. After the mixture was stirred under cooling with ice for 10 minutes, 2.5 g (0.7 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide was added thereto. After the mixture was stirred under cooling with ice for 30 minutes, the temperature was recovered to room temperature, followed by stirring for 2 hours. 30 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, subjected to filtration and purified by silica gel column chromatography to obtain 2.0 g (yield 76%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,3-dichloro-5-methoxypyridine (compound No. 193; m.p. 98-99° C.).

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice for 10 minutes
  3. stirringAfter the mixture was stirred
  4. temperatureunder cooling with ice for 30 minutes
  5. customthe temperature was recovered to room temperature
  6. stirringby stirring for 2 hours
  7. addition30 ml of water was added to the mixture
  8. customto terminate
  9. customthe reaction, and ethyl acetate
  10. additionwas added
  11. extractionfor extraction
  12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  13. filtrationsubjected to filtration
  14. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4e29c744629d4a6ba339a90cd7aeb21d
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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