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

HRID 908210

Reaction equation

HRID 908210 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, obtained by the method of Hanzlowsky et al., J. Heterocyclic Chem. 2003, 40(3), 487-498) 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. customobtained by the method of Hanzlowsky et al., J
  2. customThe solvent was evaporated
  3. washwashed (water)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c34a6319f2844cd1a5dc72ff0ff35cdc
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Linked notes

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