Benzaldehyde → 5-Benzylideneaminopyridine-2-carboxylic acid methyl ester

HRID 1680442Notes

Reaction equation

HRID 1680442 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1)=[O:4].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC=CC=1>O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 241BenzeneHCID 12457877Methyl 5-aminopyridine-2-carboxylate

Product 1

HCID 536716955-Benzylideneaminopyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 17.4 g of 5-aminopyridine-2-carboxylic acid methyl ester, 14.0 g of benzaldehyde and 100 ml of benzene is stirred and refluxed on a water separator for 6.5 hours. The resulting clear solution is evaporated, and the residue recrystallized from benzene-hexane first, then from acetonitrile-diethyl ether, to yield the 5-benzylideneaminopyridine-2-carboxylic acid methyl ester, melting at 84°-89°.

Workup

  1. customThe starting material is prepared
  2. customThe resulting clear solution is evaporated
  3. customthe residue recrystallized from benzene-hexane first

Sources & evidence

ORD record
ord-6a0602e10a9c43fda3eb694b3348d194
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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