Methylhydrazine → HCID 178439467, compound

HRID 1440744Notes

Reaction equation

HRID 1440744 reaction equation
[C:1]([CH2:6][C:7]([O:9]CC)=O)(=O)[CH:2]([CH3:4])[CH3:3].[CH3:12][NH:13][NH2:14]>C(O)C>[OH:9][C:7]1[N:13]([CH3:12])[N:14]=[C:1]([CH:2]([CH3:4])[CH3:3])[CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 178439467HCID 178439467, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 30.0 grams of ethyl isobutyrylacetate in 130 ml of ethanol (anhydrous, 5% methanol) at 10° C. was added dropwise over 30 minutes a solution of 8.7 grams of methyl hydrazine in 30 mls of ethanol. The reaction temperature did not exceed 20° C. After twenty minutes of additional stirring the cooling bath was removed and 2 ml of glacial acetic acid was added. After one hour of stirring at room temperature the reaction was then refluxed for four hours. After stirring overnight at room temperature the reaction was concentrated to yield a yellowish solid. This solid was stirred with 100 ml of hexanes for 30 minutes and the off-white solid was collected and rinsed with 75 ml of hexanes. The solid was dried in a vacuum oven at 45° C. overnight to yield 23.3 g of the desired product, mp 120°-122° C.

Workup

  1. customdid not exceed 20° C
  2. customwas removed
  3. addition2 ml of glacial acetic acid was added
  4. stirringAfter one hour of stirring at room temperature the reaction
  5. temperaturewas then refluxed for four hours
  6. stirringAfter stirring overnight at room temperature the reaction
  7. concentrationwas concentrated
  8. customto yield a yellowish solid
  9. customthe off-white solid was collected
  10. washrinsed with 75 ml of hexanes
  11. customThe solid was dried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-38be41bff32c4870b01c35efb3643ec1
Source dataset
uspto-grants-1996_03
Patent number
US05500405

Reaction notes

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