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

HRID 340216
Notes
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Reaction equation

HRID 340216 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

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-60b799d726c742ca8d4da0ea1566b81f
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895577B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes