Hydrochloric Acid → 3,4-diethyl 1H-pyrazole-3,4-dicarboxylate

HRID 1958327

Reaction equation

HRID 1958327 reaction equation
Cl.O.[NH2:3]N.Cl.[CH2:6]([O:8][C:9](=[O:22])[C:10](=[CH:18][N:19](C)C)[C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:7]>C(O)C>[CH2:15]([O:14][C:12]([C:11]1[NH:3][N:19]=[CH:18][C:10]=1[C:9]([O:8][CH2:6][CH3:7])=[O:22])=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22250811Hydrazine monohydrate hydrochlorideHCID 72733183Diethyl 2-((dimethylamino)methylene)-3-oxosuccinate

Product 1

HCID 145056993,4-diethyl 1H-pyrazole-3,4-dicarboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Under an atmosphere of argon, hydrazine monohydrate hydrochloride (1.91 g, 28 mmol) and HCl (36.5% in water, 2.8 ml) were added to a solution of 2-dimethylaminomethylene-3-oxo-succinic acid diethyl ester (6.8 g, 28 mmol) in ethanol (100 ml). The mixture was heated to 60° C. (3 h). The solvent was evaporated, and the residue was taken up in dichloromethane and washed (water). The organic layer was dried (Na2SO4), the solvent was evaporated and the title compound (1.81 mg, 31%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=383.3 [M+H+].

Workup

  1. customThe solvent was evaporated
  2. washwashed (water)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b3bf88598dd54aedbaeccee6e6f5ec2f
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Linked notes

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