Water → HCID 13373238, compound

HRID 1589526Notes

Reaction equation

HRID 1589526 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][Si:8]([CH3:18])([CH3:17])[C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.[Cl:19][C:20]1[C:21](=[O:29])[N:22]([CH2:27][CH3:28])[N:23]=[CH:24][C:25]=1[OH:26].O>CN(C)C=O>[Cl:19][C:20]1[C:21](=[O:29])[N:22]([CH2:27][CH3:28])[N:23]=[CH:24][C:25]=1[O:26][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([Si:8]([CH3:18])([CH3:17])[CH3:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12583976HCID 12583976, compoundHCID 546807714-Chloro-2-ethyl-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 13373238HCID 13373238, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 g of anhydrous potassium carbonate and 2.1 g of p-trimethylsilylbenzylbromide were added to 1.5 g of 4-chloro-2-ethyl-5-hydroxy-3(2H)-pyridazinone dissolved in 10 ml of N,N-dimethylformamide, and the resulting mixture was heated in an oil bath of 120°-130° C. for 2 hours. After the reaction mixture was allowed to cool to room temperature, 100 ml of water was added thereto and the mixture was stirred vigorously. Precipitate was filtered, washed with water and dried to obtain 1.7 g of a crude product. The product was recrystallized from a mixed solvent of isopropyl ether and ethyl acetate to obtain the intended compound (Compound No. 4.6) having m.p. 122°-125° C. (yield: 44.8%).

Workup

  1. temperaturethe resulting mixture was heated in an oil bath of 120°-130° C. for 2 hours
  2. filtrationPrecipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a4c45bc34b0e44118359ab09aaddc19f
Source dataset
uspto-grants-1986_02
Patent number
US04571397

Reaction notes

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