Methanol → methyl 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate

HRID 1413226Notes

Reaction equation

HRID 1413226 reaction equation
O=O.[CH3:3][N:4]1[C:8]([CH3:9])=[C:7](C(O)C(Cl)(Cl)Cl)[C:6](=[O:16])[N:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na].[C:24](=[O:27])(O)[O-:25].[Na+].[CH3:29]O>S(=O)(=O)(O)O.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[CH3:3][N:4]1[C:8]([CH3:9])=[C:7]([C:24]([O:25][CH3:29])=[O:27])[C:6](=[O:16])[N:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 887Methanol2×HCID 977OxygenHCID 516892Sodium BicarbonateHCID 42270691,5-Dimethyl-2-phenyl-4-(2,2,2-trichloro-1-hydroxyethyl)-1,2-dihydro-3H-pyrazol-3-oneHCID 5360545Sodium

Product 1

HCID 20294053methyl 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 212261,10-Phenanthroline hydrateCatalystHCID 1118Sulfuric AcidSolvent

Procedure

A stream of dry oxygen was passed through a stirred suspension heated at 30° C.) of 1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one-4-yl)-2,2,2-trichloroethanol (3,35 g; 10 m. moles) in methanol (15 ml) and a solution of cupric chloride dihydrate (0.025 g; 0.15 m. mole) and 1,10-phenanthroline hydrate 0.075 g; 0.38 m. mole) in methanol (15 ml) in which sodium (0.27 g; 11.7 m. moles) had been dissolved was added portionwise over a period of 60 minutes. The reaction was allowed to proceed for a further 60 minutes, the reaction mixture diluted with dilute sulphuric acid and adjusted to pH 6.0-6.5 by addition of aqueous sodium bicarbonate. The mixture was extracted with chloroform (3×50 ml), the combined extracts washed with saturated aqueous sodium carbonate (10 ml), dried (MgSO4) and evaporated to give methyl 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one-4-carboxylate (2.15 g; 87%). The product was recrystallised from acetone to give material, m.p. 154°-157° C.

Workup

  1. additionwas added portionwise over a period of 60 minutes
  2. extractionThe mixture was extracted with chloroform (3×50 ml)
  3. washthe combined extracts washed with saturated aqueous sodium carbonate (10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-939c2e8a87fc4a539103d98b4261a259
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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