Hydrochloric Acid → 2-(4-Chlorophenyl)-4-methyl-5-trifluoromethylpyridazin-3-one

HRID 2289846Notes

Reaction equation

HRID 2289846 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([C:15]#N)=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[Mg]Br.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([C:17]([F:19])([F:18])[F:20])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10946495HCID 10946495, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 110661462-(4-Chlorophenyl)-4-methyl-5-trifluoromethylpyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After 3.0 g of 2-(4-chlorophenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-15) is dissolved in 30 mL of anhydrous tetrahydrofuran, 4.0 mL of methylmagnesium bromide (3.0M diethyl ether solution) is dropped to the tetrahydrofuran solution at 0° C. and stirred for hour. Afterwards, the reaction solution is poured into diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed, in order, with water and aqueous saturated sodium chloride. After drying over anhydrous magnesium sulfate and concentrated, the residue is subjected to silica gel column chromatography to afford 2-(4-chlorophenyl)-4-methyl-5-trifluoromethylpyridazin-3-one.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed, in order, with water and aqueous saturated sodium chloride
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-679dbeea1bba41758228ef3354bce50d
Source dataset
uspto-grants-2000_07
Patent number
US06093818

Reaction notes

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