Hydrochloric Acid → 2-(2-Fluoro-4-chloro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[C:16]([C:19]#N)=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=[N:13]2)=[C:4]([F:25])[CH:3]=1.C(OCC)C.C[Mg]I.Cl>O1CCCC1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[C:16]([CH3:19])=[C:15]([C:21]([F:23])([F:22])[F:24])[CH:14]=[N:13]2)=[C:4]([F:25])[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
After 1.035 g of 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-5) was dissolved in 6.0 mL of tetrahydrofuran, 3.1 mL of a diethyl ether solution of methylmagnesium iodide (0.98M diethyl ether solution) was added to the tetrahydrofuran solution at 0° C. and stirred for 20 min under a nitrogen stream. Afterwards, the reaction solution was poured into 3N-hydrochloric acid and extracted with ethyl acetate. After the organic solvent was washed with aqueous saturated sodium bicarbonate and concentrated, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane=1/9) to afford 0.467 g of 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one (compound 2-5).
Workup
- extractionextracted with ethyl acetate
- washAfter the organic solvent was washed with aqueous saturated sodium bicarbonate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a0734779439f4634a4bb176e36b7c854
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093818
Reaction notes
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