Benzylamine → 1-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one

HRID 1866867Notes

Reaction equation

HRID 1866867 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH2:10]([N:17]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 546786591-benzyl-4-hydroxy-6-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-hydroxy-6-methyl-2-pyrone (0.2 mol, 25.2 g) and benzylamine (0.2 mol, 21.4 g) were added to water (800 mL) and heated to reflux with stirring for 2 hours. After cooling to room temperature, a light brown solid was collected by filtration. (33.4 g, 77%): 1H NMR (DMSO-d6/300 MHz) δ: 10.5 (s, 1H), 7.4-7.1 (m, 5H), 5.8-5.6 (m, 2H), 5.2 (s, 2H), 5.1 (s, 2H), 2.2 (s, 3H). ESHRMS m/z 216.100 (M+H, C12H13NO2 requires 216.102).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. filtrationa light brown solid was collected by filtration

Sources & evidence

ORD record
ord-056f945db1a84138974a66060ba10677
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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