6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide → 1-(6-Chloropyridazin-3-yl)ethan-1-one

HRID 1046069Notes

Reaction equation

HRID 1046069 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](N(OC)C)=[O:9])=[CH:4][CH:3]=1.[CH3:14][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](=[O:9])[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 584852976-chloro-N-methoxy-N-methylpyridazine-3-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 468356481-(6-Chloropyridazin-3-yl)ethan-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide (13.5 g, 0.0659 mol) in THF (600 mL) was added CH3MgBr (43.2 ml, 0.13 mol) at −78° C. under N2. The reaction mixture was stirred at −78° C. for 2 h, quenched by addition of aq NH4Cl and filtered. The filtrate was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed under vacuum, and the residue was purified by column chromatography to afford 1-(6-chloropyridazin-3-yl)ethanone. (9.3 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 8.03 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 2.81 (s, 3H).

Workup

  1. customquenched by addition of aq NH4Cl
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-feeb478af4ea436d82b1a8cfcfe7b5ea
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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