Sodium Chloride → 1-(Pyridazin-4-yl)ethan-1-one

HRID 2092016Notes

Reaction equation

HRID 2092016 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][N:9]=[N:8][CH:7]=1)=[O:5].[CH3:13][Mg]Br.[Cl-].[Na+]>O1CCCC1>[N:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH3:13])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 59574572N-Methoxy-N-methylpyridazine-4-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 144520051-(Pyridazin-4-yl)ethan-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-methoxy-N-methylpyridazine-4-carboxamide (1.13 g, 6.76 mmol) in tetrahydrofuran (22 mL), methylmagnesium bromide (10.1 mL, 10.1 mmol, 1M in diethyl ether) was added dropwise at 0° C. in a nitrogen stream, and the resulting solution was stirred for 1 hour. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium chloride and extracted with chloroform, and the extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2→0/1) to give the desired product (42% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2→0/1)

Sources & evidence

ORD record
ord-b192313b8b12471b9e30334c74e0da97
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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