Chlorosuccinimide → HCID 136359764, compound

HRID 1405996Notes

Reaction equation

HRID 1405996 reaction equation
[F:1][C:2]1[C:3]([CH:8]=[N:9][OH:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[F:1][C:2]1[C:3]([C:8]([Cl:11])=[N:9][OH:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 136359763HCID 136359763, compound

Product 1

HCID 136359764HCID 136359764, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-fluoropicolinaldehyde oxime (1.0 g, 7.1 mmol) in DMF (15.8 mL) was added N-chlorosuccinimide (1.05 g, 7.85 mmol). The r×n was heated to 50° C. After 30 min, the r×n was added to ice water and extracted with EtOAc. The collected organic layers were washed with H2CO (2×50 mL), brine (30 mL), dried (MgSO4) and filtered. Concentration provided 3-fluoro-N-hydroxypicolinimidoyl chloride as a yellow solid, which was taken through to the next step.

Workup

  1. extractionextracted with EtOAc
  2. washThe collected organic layers were washed with H2CO (2×50 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationConcentration

Sources & evidence

ORD record
ord-0433a0f98a14432c9a0309380472f7a7
Source dataset
uspto-grants-2014_12
Patent number
US08916584B2

Reaction notes

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