Ethyl Acetate → HCID 21706520, compound

HRID 1005417Notes

Reaction equation

HRID 1005417 reaction equation
[C:1]([C:3]1[C:4](=[O:10])[NH:5][N:6]=[CH:7][C:8]=1[CH3:9])#[N:2].[H-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.C(OCC)(=O)C>CN(C=O)C.O>[C:1]([C:3]1[C:4](=[O:10])[N:5]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:6]=[CH:7][C:8]=1[CH3:9])#[N:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 12376257HCID 12376257, compound

Product 1

HCID 21706520HCID 21706520, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-cyano-5-methyl-3-pyridazinone (P. Schmidt and J. Druey, Helvetica Chemica Acta, 37, 1467 (1954)) (0.93 g, 6.9 mmol) and NaH (50% in oil, 0.344 g, 8.6 mmol) in DMF (15 mL) was stirred at rt for 1 hour. 4-Methoxybenzyl chloride (1.34 g, 8.6 mmol) was added, and the mixture was stirred for 16 hours. The mixture was diluted with water, and extracted with ethyl acetate. The organic phase was washed with water, dried, filtered and evaporated. Trituration of the residue with ethyl acetate gave 4-cyano-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.83 g, 3.2 mmol, 46%).

Workup

  1. stirringthe mixture was stirred for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ea3b4436865542b78528ccddd52756e2
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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