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

HRID 1479503

Reaction equation

HRID 1479503 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-ddb48108a37b42bfb6ba2de23a944441
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Linked notes

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