Hydrochloric Acid → 5-Nitro-2-hydroxybenzophenone oxime
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)([O-:3])=[O:2].Cl.[NH2:20][OH:21].Cl>[OH-].[K+]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([CH:17]=1)[C:9](=[N:20][OH:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:3])=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into an autoclave, were charged 30 g of 2-chloro-5-nitrobenzophenone, 300 ml of water, and 9.70 g of potassium hydroxide. The mixture was allowed to react at 150° to 160° C. with stirring for 5 hours. Upon cooling to room temperature, there was obtained a clear liquid, reddish orange in color. The liquid was further cooled below 0° C. and strongly acidified with cold concentrated hydrochloric acid. The precipitated solids were collected by filtration, washed with water, and recrystallized from ethanol to yield 15.7 g (56.1%) of 5-nitro-2-hydroxy-benzophenone having a melting point of 122°-123° C. To 150 ml of 40-% aqueous potassium hydroxide solution, was added 25.0 g of 5-nitro-2-hydroxybenzophenone followed by 50 g of hydroxylamine hydrochloride. After 5 hours, the resulting clear liquid was cooled and acidified with concentrated hydrochloric acid to form a precipitate. The precipitate was washed with water and a small volume of 50-% aqueous methanol, then dried in air, and recrystallized from benzene and petroleum ether to yield 5-nitro-2-hydroxybenzophenone oxime.
Workup
- temperaturethe resulting clear liquid was cooled
- customto form a precipitate
- washThe precipitate was washed with water
- dry with materiala small volume of 50-% aqueous methanol, then dried in air
- customrecrystallized from benzene and petroleum ether
Sources & evidence
- ORD record
- ord-0a6fdccfed1d47dd8b55cd0832f16062
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04559172
Reaction notes
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