Hydrazine → HCID 178469921, compound

HRID 1520192Notes

Reaction equation

HRID 1520192 reaction equation
C[N:2]([CH:4]=[C:5]([C:11](=O)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:17]N>CCO>[CH2:12]([C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][NH:2][N:17]=1)[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 78131927Ethyl 2-((dimethylamino)methylene)-5-methyl-3-oxohexanoate

Product 1

HCID 178469921HCID 178469921, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to Scheme 1 Step 2: A solution of ethyl 2-((dimethylamino)methylene)-5-methyl-3-oxohexanoate (11.6 mmol, 2.64 g) and hydrazine (11.6 mmol, 1.47 mL) in EtOH (10 mL) was stirred for 1 hour at room temperature. After evaporation of the solvent, the resulting crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (80:20) as eluent to yield ethyl 3-isobutyl-1H-pyrazole-4-carboxylate (8.66 mmol, 1.70 g, 75%) as a yellow oil.

Workup

  1. customAfter evaporation of the solvent
  2. customthe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-6041aa7637ea4fd48093269f4b0bb3c9
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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