Triethylamine → Napthylmethylaminopyridone

HRID 1032989Notes

Reaction equation

HRID 1032989 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

5

Reactant 3

HCID 8471TriethylamineHCID 703202-BromomethylnaphthaleneHCID 4810223-Amino-5-ethyl-6-methyl-1H-pyridin-2-one

Product 1

HCID 53893567NapthylmethylaminopyridoneYield 47.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated under reduced pressure (15 torr)
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-eef5d0e6cfba422ca871ffaa9288b788
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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