Hydrochloric Acid → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-methoxy-4,5-dimethylpyridine
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:6]=1[C:7]([C:9]1[C:10](F)=[N:11][CH:12]=[C:13]([CH3:16])[C:14]=1[CH3:15])=[O:8].[OH2:27].Cl.[CH3:29]O>>[CH3:3][O:4][C:5]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:6]=1[C:7]([C:9]1[C:10]([O:27][CH3:29])=[N:11][CH:12]=[C:13]([CH3:16])[C:14]=1[CH3:15])=[O:8]Participants
Procedure
A solution having 0.06 g (1.5 mmol) of 60% sodium hydride dissolved in 1 ml of methanol, was dropwise added to a solution having 0.20 g (0.60 mmol) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridine obtained in Step (d) dissolved in 2.5 ml of methanol, followed by reflux with heating for 16 hours. After cooling to room temperature, 5 ml of water was added, and diluted hydrochloric acid was added to bring the solution weakly acidic. After extraction with ethyl ether, washing with a sodium chloride solution was carried out, and the organic layer was dried over magnesium sulfate and subjected to filtration, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain 89.0 mg (yield: 43%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-methoxy-4,5-dimethylpyridine.
Workup
- additionwas dropwise added to a solution
- temperatureby reflux
- temperaturewith heating for 16 hours
- extractionAfter extraction with ethyl ether
- washwashing with a sodium chloride solution
- dry with materialthe organic layer was dried over magnesium sulfate
- filtrationsubjected to filtration
- distillationthe solvent was distilled off under reduced pressure
- customthe obtained crude product
- customwas purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-0d34424dc7bb4cc6a9bc0f2e8ee7c238
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653277B2
Reaction notes
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