Hydrochloric Acid → 1H-Pyrazole-3,5-dicarboxylic acid, 4-hydroxy-, 3,5-diethyl ester

HRID 1977454Notes

Reaction equation

HRID 1977454 reaction equation
[CH3:1][O-:2].[Na+].C[C:5](C)(C([O-])=O)[C:6]([O-])=[O:7].[CH2:13]([O:15][C:16](=[O:20])[CH:17]=[N+:18]=[N-:19])[CH3:14].Cl.[C:22](=O)(O)[O-].[Na+].[CH3:27][OH:28]>O>[C:1]([C:5]1[C:6]([OH:7])=[C:17]([C:16]([O:15][CH2:13][CH3:14])=[O:20])[NH:18][N:19]=1)([O:28][CH2:27][CH3:22])=[O:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12192Ethyl diazoacetateHCID 516892Sodium BicarbonateHCID 6946994DimethylmalonatHCID 10942334Sodium Methoxide

Product 1

HCID 547254921H-Pyrazole-3,5-dicarboxylic acid, 4-hydroxy-, 3,5-diethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methoxide (18.9 g, 0.35 moles) was suspended in methanol (400 ml) at 5° C. Dimethylmalonate (46.2, 0.35 moles) and ethyldiazoacetate (20 g, 0.175 moles) was added quickly and the reaction stirred at room temperature for 72 hours. The reaction was cooled to 5° C. and hydrochloric acid (70 ml of 5M) added; followed by 500 ml of water. The pH of the reaction was adjusted to 7 with sodium bicarbonate and the solids (22 g, 63%) collected by filtration. EA, MS

Workup

  1. temperatureThe reaction was cooled to 5° C.
  2. filtrationthe solids (22 g, 63%) collected by filtration

Sources & evidence

ORD record
ord-be50c0de53c34087ad470915acdebc99
Source dataset
uspto-grants-2001_05
Patent number
US06232337B1

Reaction notes

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