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

HRID 1479502Notes

Reaction equation

HRID 1479502 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-4a6c8bcf0e1a4a4996b2fbb087bb2b13
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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