2-Acetylpyridine → ethyl N-(1-pyridin-2-ylethylideneamino)carbamate

HRID 1085944Notes

Reaction equation

HRID 1085944 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH2:10]([O:12][C:13](=[O:16])[NH:14][NH2:15])[CH3:11]>C(O)C>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:1](=[N:15][NH:14][C:13]([O:12][CH2:10][CH3:11])=[O:16])[CH3:2]

Participants

4

Reactant 2

HCID 142862-AcetylpyridineHCID 20064Hydrazinecarboxylic acid, ethyl ester

Product 1

HCID 2841596ethyl N-(1-pyridin-2-ylethylideneamino)carbamateYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.06 gm (0.05 mole) of 2-acetylpyridine, 5.21 gm (0.05 mole) of ethylcarbazate and 100 ml of absolute ethanol is refluxed 2 hr. The hot solution is filtered. The filtrate is cooled to room temperature and then chilled in the refrigerator. The product is collected, washed with Skellysolve B and dried to yield 3.8 gm (37%) of the title compound having a melting point of 113.2° C.

Workup

  1. temperatureis refluxed 2 hr
  2. filtrationThe hot solution is filtered
  3. temperaturechilled in the refrigerator
  4. customThe product is collected
  5. washwashed with Skellysolve B
  6. customdried

Sources & evidence

ORD record
ord-f07bdfe343024265a156e41ae8450337
Source dataset
uspto-grants-1991_04
Patent number
US05011932

Reaction notes

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