Ammonia → 5-AMINO-6-CHLORO-2(TRIFLUOROMETHYL)-1H-IMIDAZO [4,5-b] PYRIDINE
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10](OC)[C:9]([C:13]([F:16])([F:15])[F:14])=[N:8][C:5]2=[N:6][CH:7]=1.[NH3:17]>CO>[NH2:17][C:7]1[N:6]=[C:5]2[N:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[NH:10][C:4]2=[CH:3][C:2]=1[Cl:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 2.5 g. portion of 6-chloro-1-methoxy-2-(trifluoromethyl)-1-H-imidazo [4,5-b] pyridine was dissolved in 25 ml. of methanol, and the solution was saturated with gaseous ammonia. The reaction mixture was stirred at ambient temperature for 2 hours, and additional ammonia was periodically bubbled through the liquid phase. The solvent was then removed under vacuum, and the solid residue was taken up in ethyl ether and the solution was stirred with anhydrous magnesium sulfate and charcoal. The solids were then removed by filtration, and the filtrate was evaporated to dryness to yield about 2 g. of 5-amino-6-chloro-2-(trifluoromethyl)-1H-imidazo [4,5-b] pyridine, which was recrystallized from chloroform-methanol. The purified product melted at 241° -242° C. , and it was identified conclusively by infrared, nuclear magnetic resonance, mass spectroscopy and elemental microanalysis. The analytical results were as follows.
Workup
- customadditional ammonia was periodically bubbled through the liquid phase
- customThe solvent was then removed under vacuum
- stirringthe solution was stirred with anhydrous magnesium sulfate and charcoal
- customThe solids were then removed by filtration
- customthe filtrate was evaporated to dryness
- customto yield about 2 g
- customof 5-amino-6-chloro-2-(trifluoromethyl)-1H-imidazo [4,5-b] pyridine, which was recrystallized from chloroform-methanol
- customThe analytical results
Sources & evidence
- ORD record
- ord-3e2365c1ddb149788188ec2e3e5d7051
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031107
Reaction notes
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