Pyridinioacetohydrazide chloride → N-[(E)-[(E)-3-phenylprop-2-enylidene]amino]-2-pyridin-1-ium-1-ylacetamide chloride

HRID 1644169Notes

Reaction equation

HRID 1644169 reaction equation
[Cl-:1].[NH:2]([C:4](=[O:12])[CH2:5][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:3].[CH:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[CH:21]=O)=[CH:15][CH:14]=1>C(O)C>[Cl-:1].[O:12]=[C:4]([NH:2]/[N:3]=[CH:21]/[CH:20]=[CH:19]/[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)[CH2:5][N+:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 70773Pyridinioacetohydrazide chlorideHCID 637511Cinnamaldehyde

Product 1

HCID 87146327N-[(E)-[(E)-3-phenylprop-2-enylidene]amino]-2-pyridin-1-ium-1-ylacetamide chlorideYield 21.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4a (1.5 g, 8.0 mmol) and trans cinnamic aldehyde (1.6 g, 12.0 mmol) in ethanol (20 ml) was heated under reflux for 3 h. After cooling to room temperature, the mixture was filtered, and the residue dried under vacuum (0.6 mbar) to give 0.51 g (21%) of a pale-yellow solid consisting of two isomers with respect to the amide bond conformation (E:Z ca. 3:1).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. filtrationthe mixture was filtered
  4. customthe residue dried under vacuum (0.6 mbar)

Sources & evidence

ORD record
ord-3bdb95ddcf3e4914a3e2ba2b5c4466db
Source dataset
uspto-grants-2012_02
Patent number
US08124578B2

Reaction notes

Loading…