Isoamyl Nitrite → 1,3-Dimethyl-4-hydroximino-pyrazolin-5-one
Reaction equation
[N:1](OCCC(C)C)=[O:2].[CH3:9][N:10]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[NH:11]1.C[O-].[Na+]>C(O)C>[CH3:9][N:10]1[C:14](=[O:15])[C:13](=[N:1][OH:2])[CH:12]([CH3:16])[NH:11]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
183 g (1.56 mol) of isopentyl nitrite are added dropwise to 175 g (1.56 mol) of 1,3-dimethyl-pyrazolin-5-one and 84.4 g (1.56 mol) of sodium methylate in 1 L of absolute ethanol, while stirring and cooling with ice so that the internal temperature does not rise above 25° C. to 30° C. When the addition has ended, stirring is continued at room temperature for 24 hours and the sodium salt of 1,3-dimethyl-4-hydroximino-pyrazolin-5-one which has precipitated is filtered off with suction. The crystalline product is dissolved in 1 L of water and the solution is acidified with glacial acetic acid. For complete precipitation, the mixture is cooled at 0° C. for several hours, and the product is then filtered off with suction. 162 g (74% of theory) of 1,3-dimethyl-4-hydroximino-pyrazolin-5-one of melting point 93° C. are obtained.
Workup
- temperaturecooling with ice so that the internal temperature
- customdoes not rise above 25° C. to 30° C
- additionWhen the addition
- stirringstirring
- customthe sodium salt of 1,3-dimethyl-4-hydroximino-pyrazolin-5-one which has precipitated
- filtrationis filtered off with suction
- dissolutionThe crystalline product is dissolved in 1 L of water
- customFor complete precipitation
- filtrationthe product is then filtered off with suction
Sources & evidence
- ORD record
- ord-2b5aad17f4de49e2bc35aebe411c87f5
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04666933
Reaction notes
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