Hydrazine hydrate (1:1) → 5-Methyl-1H-imidazole-4-carbohydrazide

HRID 1252365Notes

Reaction equation

HRID 1252365 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]CC)=O.O.[NH2:13][NH2:14]>C(O)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([NH:13][NH2:14])=[O:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 99200Ethyl 4-methyl-5-imidazolcarboxylate

Product 1

HCID 129532705-Methyl-1H-imidazole-4-carbohydrazideYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot solution of 154 g of 5-methyl-1H-imidazole-4-carboxylic acid, ethyl ester in 2 liters of absolute ethanol was added dropwise, but rapidly, 100 g of hydrazine hydrate. The solution was stirred at reflux temperature for 3 hours, then 150 ml of hydrazine hydrate was added and the solution was refluxed for 3 days. The mixture was partially evaporated, the solid collected, washed twice with absolute ethanol, then ether and dried, giving 121.3 g of 5-methyl-1H-imidazole-4-carboxylic acid hydrazide.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. temperaturethe solution was refluxed for 3 days
  3. customThe mixture was partially evaporated
  4. customthe solid collected
  5. washwashed twice with absolute ethanol
  6. dry with materialether and dried

Sources & evidence

ORD record
ord-849b72928f5c42ba9ce1db90a538a00d
Source dataset
uspto-grants-1988_05
Patent number
US04743586

Reaction notes

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