Potassium Carbonate → 7-Chloro-1-methyl-[1]-benzopyrano[2,3-c]pyrazol-4-on

HRID 637597Notes

Reaction equation

HRID 637597 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:18])[C:16]=1[OH:17])=[O:11]>CN(C)C=O>[Cl:23][C:21]1[CH:20]=[CH:19][C:9]2[C:10](=[O:11])[C:12]3[CH:13]=[N:14][N:15]([CH3:18])[C:16]=3[O:17][C:8]=2[CH:22]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178481842HCID 178481842, compound

Product 1

HCID 135640747-Chloro-1-methyl-[1]-benzopyrano[2,3-c]pyrazol-4-onYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.38 g (0.01 mol) of potassium carbonate was added to 2.71 g (0.01 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole dissolved in 20 ml of N,N-dimethylformamide, and the reaction mixture was stirred at 100°-120° C. for 5 hours. After cooling, the reaction mixture was poured into ice water, and extracted with chloroform. The chloroform layer was dried and the solvent was distilled off under reduced pressure to obtain a solid product. It was recrystallized from methanol to obtain 2.15 g of the title compound as colorless needle crystals (yield: 92%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a solid product
  6. customIt was recrystallized from methanol

Sources & evidence

ORD record
ord-043aa7a62a9749cf9a904d656380e76a
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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