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

HRID 12256

Reaction equation

HRID 12256 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%). 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-81533076c8b148cfa53adb9113171694
Source dataset
uspto-grants-2010_06
Patent number
US07727992B2

Linked notes

Loading…