Acetone → 5-methyl-3,6-diphenylisoxazolo[4,5-c]pyridin-4(5H)-one
Reaction equation
CC(C)=O.N[C:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[C:19]([NH:21][CH3:22])=[O:20].Cl>O>[CH3:22][N:21]1[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=2[C:19]1=[O:20]Participants
Procedure
Under a nitrogen atmosphere, there is added 54 liters of acetone to 5.4 kilograms (16.9 mole) of 5-(2-amino-2-phenylethenyl)-N-methyl-3-phenyl-isoxazole-4-carboxamide at room temperature. To the resulting suspension, there is added 10.8 liters of approximately 5N hydrochloric acid while maintaining the temperature below 25° C. The mixture is then stirred overnight at 25° to 28° C. The resulting suspension is diluted with 16 liters of water at room temperature, and after mixing for 15 minutes, the solids are then filtered off and washed three times with a mixture of acetone/water (2:1). The resulting solids are then dried under reduced pressure at 45° C. to obtain 3.86 kilograms of 5-methyl-3,6-diphenyl-isoxazolo[4,5-c]pyridine-4(5H)-one; m.p. 145° to 148° C. The mother liquor is then concentrated under reduced pressure maintaining the temperature below 50° C. The mother liquor is then cooled to 20° C., the solids filtered off and washed three times with acetone/water (2:1) to obtain a second crop of 290 grams of 5-methyl-3,6-diphenyl-isoxazolo[4,5-c]pyridine-4(5H)-one; m.p. 140° to 145° C.; Yield 81%.
Workup
- temperaturewhile maintaining the temperature below 25° C
- additionafter mixing for 15 minutes
- filtrationthe solids are then filtered off
- washwashed three times
- additionwith a mixture of acetone/water (2:1)
- customThe resulting solids are then dried under reduced pressure at 45° C.
Sources & evidence
- ORD record
- ord-39b481c6c9744507abccfdd3dd37b6e9
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04154928
Reaction notes
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