Pyridine → N-hydroxybenzenecarboximidoyl chloride

HRID 1375628Notes

Reaction equation

HRID 1375628 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:16]N1C(=O)CCC1=O.[Na+].[Cl-]>C(Cl)(Cl)Cl>[Cl:16][C:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide

Product 1

HCID 2756315N-hydroxybenzenecarboximidoyl chlorideYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To benzaldehyde oxime (12.2 g, 0.1 mol) in chloroform was added catalytic amount of pyridine, followed by N-chlorosuccinimide (13.35 g, 0.1 mol) at room temperature. The reaction mixture was stirred for 1.5 h, then saturated aqueous NaCl was added. The organic phase was washed with saturated aqueous NaCl (twice) and dried with MgSO4. The solvent was removed under reduced pressure. 13.85 g α-chlorobenzaldehyde oxime was obtained. The yield was 87%.

Workup

  1. washThe organic phase was washed with saturated aqueous NaCl (twice) and
  2. dry with materialdried with MgSO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e0e02c3fab8641aa9493a4ffcbcf26b0
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Reaction notes

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