4-Methoxybenzylamine → HCID 54688158, compound

HRID 1866944Notes

Reaction equation

HRID 1866944 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1>O>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:17]2[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]2=[O:9])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54688158HCID 54688158, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy-6-methyl-2-pyrone (4.60 g, 36.45 mmol) and 4-methoxybenzylamine (5.00 g, 36.45 mmol) in H2O (100 mL) were heated to reflux. After 15 hours at reflux the reaction was allowed to cool to room temperature. The precipitate was collected by filtration washing with H2O to give a pale yellow solid (8.00 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 7.2 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.7 Hz, 2H), 5.74 (d, J=2.0 Hz, 1H), 5.56 (d, J=2.5 Hz, 1H), 5.08 (s, 2H), 3.68 (s, 3H), 2.14 (s, 3H).

Workup

  1. temperatureAfter 15 hours at reflux the reaction
  2. filtrationThe precipitate was collected by filtration
  3. washwashing with H2O

Sources & evidence

ORD record
ord-01688900038e4dbb9b84284ad445df9b
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…