Methyl acetoacetate → HCID 178463089, compound

HRID 350885Notes

Reaction equation

HRID 350885 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([NH:9][NH2:10])[CH3:8].C(N(CC)CC)C.[C:18](OC)(=[O:23])[CH2:19][C:20]([CH3:22])=O>C1(C)C=CC=CC=1>[CH2:7]([N:9]1[C:18]([OH:23])=[CH:19][C:20]([CH3:22])=[N:10]1)[CH3:8]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 8471TriethylamineHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)

Product 1

HCID 178463089HCID 178463089, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 23 g of ethyl hydrazine oxalate and 22 ml of triethylamine in 500 ml of toluene was stirred at room temperature for 15 minutes. 17 ml of methyl acetoacetate was added and the mixture was azeotroped for 1.5 hours. The mixture was evaporated and the residue was purified by flash chromatography on silica gel using dichloromethane/methanol (97:3) for the elution to give 19 g of 2-ethyl-5-methyl-2H-pyrazol-3-ol as an orange solid.

Workup

  1. customthe mixture was azeotroped for 1.5 hours
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash chromatography on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-44cc6c2e22944aa5b2eb31f8fc938162
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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