Sodium Nitrate → HCID 178472904, compound
Reaction equation
[N+:1]([O-:4])([O-])=O.[Na+].[Br:6][CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>O.C(O)(=O)C>[OH:4][N:1]=[C:9]([C:8]([CH2:7][Br:6])=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
A solution of sodium nitrate (12.4 g.) in water (150 ml.) was dropwise added with stirring at 5° to 7° C. to a solution of ethyl 4-bromoacetoacetate (30 g.) in acetic acid (200 ml.) and the mixture was stirred for 2 hours at 10° C. Water (200 ml.) was added to the reaction mixture and the resultant mixture was extracted with ether (500 ml.). The extract was washed twice with water (200 ml.) and with a sodium chloride aqueous solution (200 ml.) and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give yellowish brown crystals of ethyl 2-hydroxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (32.6 g.).
Workup
- extractionthe resultant mixture was extracted with ether (500 ml.)
- washThe extract was washed twice with water (200 ml.) and with a sodium chloride aqueous solution (200 ml.)
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-33b810a2557246e4932d5bcb2fc80d5a
- Source dataset
- uspto-grants-1982_02
- Patent number
- US04316019
Reaction notes
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