Hydrochloric Acid → Chloro(2-chloro(3-pyridyl))(hydroxyimino)methane

HRID 1823264Notes

Reaction equation

HRID 1823264 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11]N1C(=O)CCC1=O.Cl>CN(C)C=O>[Cl:11][C:8]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[N:9][OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 27634542-Chloropyridine-3-carboxaldehyde oxime

Product 1

HCID 73867584Chloro(2-chloro(3-pyridyl))(hydroxyimino)methaneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2-chloropyridine-3-carboxaldehyde oxime (2.50 g, 0.016 mol) in N,N-dimethylformamide (20 mL). Add N-chlorosuccinimide (2.14 g, 0.016 mol) in small portions along with a small amount of gaseous hydrochloric acid. Stir for 3 hours. When TLC analysis indicates the reaction to be complete, pour into ice/water. Extract with diethyl ether and wash the combined extracts with water and dry over sodium sulfate. Concentrate the extracts to give 3.00 g (98%) of crude product as an off white solid. MS(FD): (M)+ 190.0, 192.0 m/z.

Workup

  1. customthe reaction
  2. extractionExtract with diethyl ether
  3. washwash the combined extracts with water
  4. dry with materialdry over sodium sulfate
  5. concentrationConcentrate the extracts

Sources & evidence

ORD record
ord-d519a7a22f3f42468e15ecf6c09d32cb
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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