2-Pyridinemethanamine → 4-Hydroxy-6-methyl-1-pyridin-2-ylmethyl-1H-pyridin-2-one

HRID 1968686Notes

Reaction equation

HRID 1968686 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:4](=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 547030554-Hydroxy-6-methyl-1-pyridin-2-ylmethyl-1H-pyridin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 12.6 g (0.1 mol) of 4-hydroxy-6-methyl-2-pyrone in 50 ml water was added 2-(aminomethyl)pyridine (10.3 ml, 0.1 mol) and the mixture heated to reflux for 2.5 hours. The resulting light yellow compound was filtered from the cooled mixture. Concentration of the filtrate and trituration of the resulting gum with dichloromethane afforded a second crop of the title compound (19.85 g, 92%). 1H NMR (DMSO-d6, ppm): 10.5 (s, 1H), 8.5 (d, 1H), 7.7-7.8 (t, 1H), 7.2 (t, 1H), 7.1 (d, 1H), 5.8 (s, 1H), 5.5 (s, 1H), 5.2 (s, 2H), 2.2 (s, 3H). FIA: m/z−215.1 ES−/217.1 ES+

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationThe resulting light yellow compound was filtered from the cooled mixture

Sources & evidence

ORD record
ord-a2d4b0cac3694e2fbaf1ddcad51505bc
Source dataset
uspto-grants-2013_04
Patent number
US08426426B2

Reaction notes

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