Hydrochloric Acid → 2-Chloro-6-ethyl-3-(3-methylbenzoyl)pyridine
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[Cl:10][C:11]1[C:16]([C:17]#N)=[CH:15][CH:14]=[C:13]([CH2:19][CH3:20])[N:12]=1.[Cl-].[NH4+].Cl.[O:24]1CCCC1>>[Cl:10][C:11]1[C:16]([C:17](=[O:24])[C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([CH3:8])[CH:5]=2)=[CH:15][CH:14]=[C:13]([CH2:19][CH3:20])[N:12]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
3-Bromotoluene (12.5 g, 73.1 mmol) was added to a tetrahydrofuran (200 ml) solution of magnesium (1.70 g, 70.0 mmol), and the mixture was stirred until magnesium pieces disappeared. The reaction solution was cooled to -20° C., mixed with 2-chloro-3-cyano-6-ethylpyridine (10.6 g, 63.6 mmol) and then stirred for 17 hours at room temperature. The reaction solution was mixed with saturated ammonium chloride aqueous solution and 1 N hydrochloric acid, and the mixture was stirred for 2 hours at room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-6-ethyl-3-(3-methylbenzoyl)pyridine (9.19 g, 56%) as a yellow oily material.
Workup
- stirringthe mixture was stirred for 2 hours at room temperature
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
- customwas removed by filtration
- concentrationthe filtrate was concentrated under a reduced pressure
- customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-f28148fc2cb842f4be863bdff7b7f5c5
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136810
Reaction notes
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