Water → Pyridine 2-aldoxime
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[OH2:9].Cl.[NH2:11]O.[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[N:11][OH:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of pyridine-2-carboxaldehyde (5.5 mL; 57.8 mmol) in ethanol (100 mL) at 0° C., was added water (22 mL) and hydroxylamine hydrochloride (5.32 g; 76.6 mmol). Aqueous sodium hydroxide (1N; 50 mL) was added dropwise and the reaction mixture warmed to room temperature overnight. The reaction mixture was poured into water (250 mL) and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water (100 mL), dried (MgSO4), filtered and evaporated to yield oxime 1e as a white solid.
Workup
- extractionextracted with ethyl acetate (3×150 mL)
- washThe combined organic layers were washed with water (100 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5ca5df5f73694851b03fd33abc9e7d5c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902227B2
Reaction notes
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