2-Hydrazinoethanol → Ethyl 1-(2-hydroxyethyl)-1H-pyrazole-4-carboxylate

HRID 2245186Notes

Reaction equation

HRID 2245186 reaction equation
[CH:1]([CH:3]([CH:9]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.[OH:11][CH2:12][CH2:13][NH:14][NH2:15]>C(O)C>[OH:11][CH2:12][CH2:13][N:14]1[CH:1]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:9]=[N:15]1

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 11029955Ethyl 2-formyl-3-oxopropanoate2×

Product 1

HCID 13062753Ethyl 1-(2-hydroxyethyl)-1H-pyrazole-4-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 5 was prepared using the classical approach for preparing pyrazoles [7]. Ethyl 2-formyl-3-oxopropionate (2.80 g; 20 mmol) was dissolved in 20 ml of ethanol and cooled to 0° C. 2-Hydroxyethylhydrazine (1.44 g; 20 mmol) was dissolved in 100 ml of ethanol and was added dropwise to the solution of ethyl 2-formyl-3-oxopropionate. The reaction mixture was left overnight at room temperature. The solvent was vacuum removed yielding a yellow oil. Yield: 95%

Workup

  1. customremoved
  2. customyielding a yellow oil

Sources & evidence

ORD record
ord-c9de7c76949a469aba2cf3210ccf0e56
Source dataset
uspto-grants-2010_03
Patent number
US07682601B2

Reaction notes

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