Water → HCID 18689486, compound

HRID 1871864Notes

Reaction equation

HRID 1871864 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[C:13]([CH3:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=[N:10]2)=[C:4]([F:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30].O>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:30][CH:29]=[CH2:28])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[C:13]([CH3:16])=[C:12]([C:17]([F:18])([F:20])[F:19])[CH:11]=[N:10]2)=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 99490912-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone2×

Product 1

HCID 18689486HCID 18689486, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 400 mg (1.2 mmol) of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-trifluoromethyl-3-oxo-2,3-dihydropyridazine (intermediate 1) was dissolved in 2.0 ml of N,N-dimethylformamide, to which 257 mg (1.86 mmol) of potassium carbonate and 165 mg (1.36 mmol) of allyl bromide were added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography, which afforded 405 mg (1.1 mmol) of 2-{4-chloro-2-fluoro-5-(2-propenyloxy)phenyl}-4-methyl-5-trifluoromethyl-3-oxo-2,3-dihydropyridazine (hereinafter referred to as intermediate 2), m.p. 79.8° C.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c674a94fb6b44c35a35620e73ab50757
Source dataset
uspto-grants-2000_08
Patent number
US06107250

Reaction notes

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