Reaction equation
[OH-].[Na+].BrBr.NC([C:8]1[C:9]([Cl:19])=[N:10][C:11]([CH3:18])=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15])=O.[NH2:20]C(C1C=NC=CC=1)=O>O>[NH2:20][C:8]1[C:9]([Cl:19])=[N:10][C:11]([CH3:18])=[CH:12][C:13]=1[C:14]([F:17])([F:16])[F:15]Participants
6
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 6.6 g of sodium hydroxide in 60 ml of water at 5° C. was added 9.3 g of bromine. When a clear solution was obtained, 9.2 g of 3-aminocarbonyl-2-chloro-6-methyl-4-(trifluoromethyl)pyridine was added quickly, maintaining the temperature below 5° C. The resulting mixture was stirred until the 3-(aminocarbonyl)pyridine dissolved (~30 min). The cooling bath was removed and the mixture was then warmed to 75° C. for 30 min. After cooling to room temperature, the 3-aminopyridine product was extracted with ethyl acetate, dried (magnesium sulfate), filtered, and evaporated to give 4.9 g of the desired product.
Workup
- customWhen a clear solution was obtained
- temperaturemaintaining the temperature below 5° C
- dissolutiondissolved (~30 min)
- customThe cooling bath was removed
- temperatureAfter cooling to room temperature
- extractionthe 3-aminopyridine product was extracted with ethyl acetate
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-d1e9210922024c1794abea3aecf6bd64
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05620974
Linked notes
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