Hydroxyamine hydrochloride → 4,6-Dichloro-5-pyrimidinecarbaldehyde oxime
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.CC([O-])=O.[Na+].[NH2:16][OH:17].Cl>CCO>[Cl:1][C:2]1[C:7]([CH:8]=[N:16][OH:17])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4,6-dichloropyrimidine-5-carbaldehyde (8.00 g, 44.8 mmol), NaOAc (3.7 g, 1.0 eq) and NH2OH.HCl (3.1 g, 1.0 eq) in EtOH (320 mL) was stirred at rt for 2 h. The reaction mixture was filtered, concd and purified by column chromatography on silica gel (dry loading, first DCM then DCM/EtOAc, 1/9) to give 4,6-dichloropyrimidine-5-carbaldehyde oxime as a white solid.
Workup
- filtrationThe reaction mixture was filtered
- customconcd and purified by column chromatography on silica gel (
- dry with materialdry loading, first DCM
Sources & evidence
- ORD record
- ord-afbae19d534f4d49a5b77e55dbfc9687
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754089B2
Reaction notes
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