Pyridine → 3-Chloro-5-(trifluoromethyl)picolinaldehyde oxime

HRID 340215

Reaction equation

HRID 340215 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[NH2:15][OH:16].N1C=CC=CC=1>C(O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([CH:12]=[N:15][OH:16])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 220187903-Chloro-5-(trifluoromethyl)picolinaldehyde

Product 1

HCID 7182493-Chloro-5-(trifluoromethyl)picolinaldehyde oxime

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-chloro-5-(trifluoromethyl)picolinaldehyde (1.0 eq.), hydroxylamine hydrochloride (5.0 eq.), and pyridine (4.0 eq.) in ethanol was heated to 95° C. and stirred for 1 hour. The reaction was cooled to room temperature and diluted with ethyl acetate and water. The organic layer was washed with brine, water, dried over anhydrous MgSO4, and concentrated en vacuo to give a solid that was carried onto the next step without further purification.

Workup

  1. washThe organic layer was washed with brine, water
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated en vacuo
  4. customto give a solid
  5. customthat was carried onto the next step without further purification

Sources & evidence

ORD record
ord-14dc081e82d34930bc4420a3d7a9cd95
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Linked notes

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