Sodium Sulfite → 1-(Imidazo[1,2-a]pyridin-6-yl)propan-2-one
Reaction equation
[CH:1]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[CH:10]=1)=[C:2](C)[CH3:3].[O:14]=[O+][O-].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>Cl.O.CO>[N:13]1[CH:12]=[CH:11][N:9]2[CH:10]=[C:5]([CH2:1][C:2](=[O:14])[CH3:3])[CH:6]=[CH:7][C:8]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -5 °C
Procedure
In a solution of 12.3 g of conc. hydrochloric acid, 45 ml of water and 45 ml of methanol was dissolved 20 g of 6-isobutenylimidazo[1,2-a]pyridine. The solution was cooled to -5° C. Ozone was introduced to the solution at -5° to 0° C. for 4 hours. The endpoint of the reaction was confirmed by thin layer chromatography. After completion of the reaction, a solution of 30.6 g of sodium sulfite in 160 ml of water was dropwise added under cooling at such a rate that the temperature did not exceed 20° C. Next, 22 g of sodium bicarbonate and an appropriate amount of salt were added as solids and the mixture was extracted with chloroform. The chloroform extract was washed twice with a saturated saline solution. After drying over magnesium sulfate, chloroform was removed by distillation under reduced pressure. The residue was purified by distillation under reduced pressure to obtain 14.2 g (70.5%) of 1-(imidazo[1,2-a]pyridin-6-yl)-2-propanone.
Workup
- customAfter completion of the reaction
- temperatureunder cooling at such a rate that the temperature
- customdid not exceed 20° C
- extractionthe mixture was extracted with chloroform
- extractionThe chloroform extract
- washwas washed twice with a saturated saline solution
- dry with materialAfter drying over magnesium sulfate, chloroform
- customwas removed by distillation under reduced pressure
- distillationThe residue was purified by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-986f491467b04e43a6b51d9080674788
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04791202
Reaction notes
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