Hydroxyamine hydrochloride → 2-Chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde oxime
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:8][N:9]=1)[CH:5]=O.C([O-])(=O)C.[Na+].Cl.[NH2:25][OH:26]>C(O)C.ClC(Cl)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:8][N:9]=1)[CH:5]=[N:25][OH:26]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 2-chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde (1.1 g, 4.0 mmol), sodium acetate (490 mg, 6 mmol), and hyroxylamine hydrochloride (415 mg, 6 mmol) in ethanol (23 mL) and dichloroethane (13 mL) was heated at 50° C. for 15 minutes. The cooled reaction mixture was evaporated in vacuo to afford a residue that was redissolved in ethyl acetate (150 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a white solid that was used in the next step without further purification.
Workup
- customThe cooled reaction mixture
- customwas evaporated in vacuo
- customto afford a residue that
- washwashed with water (100 mL)
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customto afford a white solid that
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-150dddf07c774851bcb9841ae1f580ad
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623889B2
Reaction notes
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