Perchloric Acid → O-(2,4-dinitrophenyl)hydroxylamine
Reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:5]=1[O:6][N:7]=C(OCC)C)([O-:3])=[O:2].Cl(O)(=O)(=O)=O>O1CCOCC1>[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:5]=1[O:6][NH2:7])([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 2.0 g (0.0074 mole) of ethyl N-(2,4-dinitrophenoxy)acetimidate in 10 mL of dioxane, cooled in an ice/water bath, was added dropwise 3 mL of 70% perchloric acid during a 10 minute period. The reaction mixture was stirred at 0°-5° C. for five hours and then was poured into 100 mL of ice water. This mixture was extracted three times with 40 mL of methylene chloride. The combined extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving 2.8 g of a brown oil. This oil was dissolved in 20 mL of diethyl ether, and 30 mL of petroleum ether was added to the solution, causing a precipitate to form. This precipitate was recovered by filtration. After being washed with petroleum ether and dried, 0.75 g of O-(2,4-dinitrophenyl)hydroxylamine was recovered as a yellow powder. The NMR spectrum was consistent with the proposed structure. This method is described by Y. Tamura et al., J. Org. Chem., 38, 1239 (1973).
Workup
- temperaturecooled in an ice/water bath
- extractionThis mixture was extracted three times with 40 mL of methylene chloride
- dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was evaporated from the filtrate under reduced pressure
Sources & evidence
- ORD record
- ord-8ada37e1a4cc484b8b5ad3bd24ca0ed0
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05441925
Reaction notes
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