Methylhydrazine → HCID 57446236, compound

HRID 1095369Notes

Reaction equation

HRID 1095369 reaction equation
[Na].[CH3:2][CH:3]([CH3:15])[CH2:4][C:5](=O)[CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:16][NH:17][NH2:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH2:4]([C:5]1[N:17]([CH3:16])[N:18]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=1)[CH:3]([CH3:15])[CH3:2]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 10340Sodium CarbonateHCID 86628641HCID 86628641, compound

Product 1

HCID 57446236HCID 57446236, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1 L round bottom flask was charged with ethyl 6-methyl-2,4-dioxoheptanoate sodium salt (30.0 g, 135 mmol) and acetic acid (200 mL). Methylhydrazine (7.20 mL, 135 mmol) was added dropwise via syringe, and the resultant solution was allowed to stir under a nitrogen atmosphere for 2 hours. The pH was then adjusted to 9 by addition of saturated aqueous sodium carbonate, and the reaction mixture was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to provide 27.5 g of ethyl 5-isobutyl-1-methyl-1H-pyrazole-3-carboxylate as a yellow oil. This material was utilized without any further purification.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea686823e7b043ba8dc9c3553fc14700
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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