N-chlorosuccinamide → N-Hydroxypicolinimidoyl chloride

HRID 1506443Notes

Reaction equation

HRID 1506443 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[N:8]/[OH:9].[Cl:10]NC(=O)CCC(N)=O>CN(C=O)C.C(OCC)C>[OH:9]/[N:8]=[C:7](\[Cl:10])/[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 135423666syn-2-Pyridinealdoxime

Product 1

HCID 135440287N-Hydroxypicolinimidoyl chlorideYield 62.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-picolinaldehyde oxime (10.0 g, 82.0 mmol) in DMF (30 mL) at room temperature was slowly added over 30 minutes N-chlorosuccinamide (10.9 g, 82.0 mmol). An exotherm was noted during the addition. The reaction mixture was stirred overnight at room temperature, diluted with diethyl ether (300 mL), washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with dichloromethane, and the resulting solid was collected by vacuum filtration and dried to give (Z)—N-hydroxypicolinimidoyl chloride (12.8 g, 51.1 mmol, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.49 (ddd, 1H), 7.83-7.95 (m, 2H), 8.66 (ddd, J=4.73, 1.43, 1.32 Hz, 1H), and 12.64 (s, 1H).

Workup

  1. additionAn exotherm was noted during the addition
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with dichloromethane
  6. filtrationthe resulting solid was collected by vacuum filtration
  7. customdried

Sources & evidence

ORD record
ord-24b94eb332254725b00deca2fa89b0d5
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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