Hydrazine hydrate (1:1) → Pyrimidine-2-carbohydrazide

HRID 842694Notes

Reaction equation

HRID 842694 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O)C.O.[NH2:13][NH2:14]>C(O)C>[N:7]1[CH:8]=[CH:9][CH:10]=[N:11][C:6]=1[C:4]([NH:13][NH2:14])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 133607152-Pyrimidinecarboxylic acid, ethyl ester

Product 1

HCID 11182639Pyrimidine-2-carbohydrazideYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pyrimidine-2-carboxylic acid ethyl ester (Ann. Chim., 5, 351 (1960)) (0.866 g, 5.7 mmol) and hydrazine hydrate (0.332 mL, 6.8 mmol) in ethanol (20 mL) was heated under reflux for 3 hours, then concentrated under reduced pressure. The residue was triturated with diethyl ether, collected by filtration and washed with ethyl acetate to give the title compound (0.542 g, 69%) as a yellow solid, mp 173-175° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with diethyl ether
  5. filtrationcollected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-2fa267b98ea94ae3812056f8a83e5668
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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