3-Chloro-5-(trifluoromethyl)picolinaldehyde oxime → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1259084Notes

Reaction equation

HRID 1259084 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]=[N:13]O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O1CCCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:12]#[N:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 2

HCID 7182493-Chloro-5-(trifluoromethyl)picolinaldehyde oximeHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate

Product 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-chloro-5-(trifluoromethyl)picolinaldehyde oxime (1.0 eq.) and Burgess reagent (1.5 eq.) in tetrahydrofuran (0.5 M) was heated to 65° 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 water, brine, 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 water, brine
  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-31fe597c2e2047f997456cf43dd4c7d9
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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