Chlorosuccinimide → N-hydroxy-6-methylpicolinimidoyl chloride

HRID 1948528Notes

Reaction equation

HRID 1948528 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](/[CH:8]=[N:9]/[OH:10])[CH:5]=[CH:4][CH:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[OH:10][N:9]=[C:8]([Cl:11])[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 1354417466-Methylpyridine-2-carbaldehyde oxime

Product 1

HCID 136337383N-hydroxy-6-methylpicolinimidoyl chlorideYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of commercially available (E)-6-methylpicolinaldehyde oxime (2 g, 14.69 mmol) in DMF (25 mL) was added 1-chloropyrrolidine-2,5-dione (2.158 g, 16.16 mmol). The reaction mixture was stirred overnight at room temperature. LCMS shows reaction was complete. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl (×3). The organic layer was dried with MgSO4, filtered, and concentrated to yield 2.5 g of N-hydroxy-6-methylpicolinimidoyl chloride. MS (m+1)=171. HPLC Peak RT=0.79 minutes (Analytical Method B).

Workup

  1. customreaction
  2. washwashed with saturated NaCl (×3)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48cf3075aef447df8fa48fc36bfa4cfb
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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