Water → 4-Chloro-N-hydroxy-3-pyridinecarboximidoyl chloride

HRID 1823277Notes

Reaction equation

HRID 1823277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[N:9][OH:10].[Cl:11]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:11][C:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[N:9][OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 57365610HCID 57365610, compound

Product 1

HCID 738675804-Chloro-N-hydroxy-3-pyridinecarboximidoyl chlorideYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 4-chloropyridine-3-carboxaldehyde oxime (2.60 g, 0.017 mol) in N,N-dimethylformamide (20 mL). Add N-chlorosuccinimide (2.48 g, 0.018 mol) in small portions and stir overnight at ambient temperature. Pour the mixture into water and extract with ethyl acetate. Wash the combined extracts with water and dry over sodium sulfate. Concentrate in vacuo to give 2.45 g (75%) of crude product as a yellowish solid. 1H NMR was consistent with structure.

Workup

  1. extractionextract with ethyl acetate
  2. washWash the combined extracts with water
  3. dry with materialdry over sodium sulfate
  4. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-bfd19997605e4ea5a3112a30a94f813e
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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