Methyl acetoacetate → HCID 178463089, compound

HRID 47618Notes

Reaction equation

HRID 47618 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 3.9 g of ethyl hydrazine oxalate and 3.6 ml of triethylamine in 80 ml of toluene was stirred at room temperature for 15 min. 2.8 ml of methyl acetoacetate was added and the mixture was azeotroped for 1.5 h. 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 3.1 g of 2-ethyl-5-methyl-2H-pyrazol-3-ol as an orange solid.

Workup

  1. customthe mixture was azeotroped for 1.5 h
  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-dc9105b2b9334599b979c7551c1748dd
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Reaction notes

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