Triethylamine → Napthylmethylaminopyridone

Reaction equation

[NH2:1][C:2]1[C:3](=[O:11])[NH:4][C:5](C)=[C:6](CC)[CH:7]=1.BrC[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1.[CH2:24](N(CC)CC)C>C(#N)C>[C:17]1([CH2:24][NH:1][C:2]2[C:3](=[O:11])[NH:4][CH:5]=[CH:6][CH:7]=2)[C:16]2[C:21](=[CH:22][CH:23]=[CH:14][CH:15]=2)[CH:20]=[CH:19][CH:18]=1

Participants

Procedure

A mixture of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (3.0 g, 20 mmol), 2-bromomethylnapthalene (4.4 g, 20 mmol), triethylamine (2.0 g, 20 mmol) in acetonitrile (200 mL) was heated under reflux for 4 hours. The resultant mixture was allowed to cool to room temperature and concentrated under reduced pressure (15 torr). The residue was then subjected to column chromatography on silica gel (300 g, elution with methanol-chloroform, 5:95 v/v). Collection and concentration of appropriate fractions provided 2.4 g (42%) of the napthylmethylaminopyridone.