Water → 5-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

HRID 333740Notes

Reaction equation

HRID 333740 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.C[O:9][C:10]1[C:11](=[O:28])[C:12]([C:22]2[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=2)=[N:13][N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1.O>C(#N)C>[OH:9][C:10]1[C:11](=[O:28])[C:12]([C:22]2[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=2)=[N:13][N:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 895866805-methoxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 895867585-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-oneYield 35.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of sodium iodide (7.49 g) in acetonitrile (300 mL) was added chlorotrimethylsilane (6.35 mL) at room temperature with stirring, and the mixture was stirred for 30 min. Then, 5-methoxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one (2.82 g) was added, and the mixture was stirred for 30 min at the same temperature and further refluxed for 7 hr. The reaction mixture was allowed to cool to room temperature, poured into water and the mixture was stirred for 30 min. The resulting precipitate was collected by filtration, washed successively with water, methanol, and diisopropyl ether, and dried to give the title compound (0.95 g) as pale-yellow needles. The filtrate was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (1.70 g) as pale-yellow needles.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was stirred for 30 min at the same temperature
  3. temperaturefurther refluxed for 7 hr
  4. stirringthe mixture was stirred for 30 min
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed successively with water, methanol, and diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-dc392c7cf98c445e9d348b417d95c508
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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