Chlorosuccinimide → N-hydroxy-6-methylnicotinimidoyl chloride

HRID 2101410Notes

Reaction equation

HRID 2101410 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][N:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[OH:8][N:7]=[C:6]([Cl:11])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 71325686N-[(6-Methylpyridin-3-yl)methylidene]hydroxylamine

Product 1

HCID 72574142N-hydroxy-6-methylnicotinimidoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring mixture of 6-methylnicotinaldehyde oxime (500 mg, 3.67 mmol) in 4 mL DMF at room temperature, was added N-chlorosuccinimide (490 mg, 3.67 mmol) in roughly one tenth portions over 5 min. Additional N-chlorosuccinimide (175 mg, 1.31 mmol) was added after about 4 h. After a total of 6 h, the reaction mixture was diluted with EtOAc, washed with water, brine, dried (Na2SO4) and filtered. The filtrate was passed through a short silica gel column eluted with EtOAc. The eluant was concentrated under vacuum to provide the title compound as a light brown solid. All of this was used in the next step without further purification. HPLC: retention time=0.44 min.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. washeluted with EtOAc
  5. concentrationThe eluant was concentrated under vacuum

Sources & evidence

ORD record
ord-21145f275c79428b8f63bd555f1989a9
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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