Acetylacetone → 1-(2-Methylpyridin-3-yl)ethan-1-one
Reaction equation
[NH2:1][CH:2]=[CH:3]C=O.[C:6]([CH2:9][C:10](=[O:12])[CH3:11])(=O)[CH3:7].[C:13]([O-])(=O)C.[NH4+]>C(OC(C)C)(C)C>[C:10]([C:9]1[C:2]([CH3:3])=[N:1][CH:13]=[CH:7][CH:6]=1)(=[O:12])[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a mixture of 3-amino acrolein (4.52 g) and acetylacetone (7.64 g) was added catalytic amount of ammonium acetate. The mixture was heated for 19 hours at ca. 110° C., After cooling to room temperature, the mixture was poured into 100 ml of isopropyl ether and dried over magnesium sulfate. The resultant mixture was filtered off by suction in vacuo to remove an insoluble material and the filtrate was concentrated in vacuo. The crude compound was purified by column chromatography on silica gel with chloroform to give 3-acetyl-2-methylpyridine (3.58 g) as a yellow oil.
Workup
- temperatureAfter cooling to room temperature
- dry with materialdried over magnesium sulfate
- filtrationThe resultant mixture was filtered off by suction in vacuo
- customto remove an insoluble material
- concentrationthe filtrate was concentrated in vacuo
- customThe crude compound was purified by column chromatography on silica gel with chloroform
Sources & evidence
- ORD record
- ord-cd27a19dab5c473b8b55a2d2c91e770a
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05763437
Reaction notes
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