Ammonium → 2-(Hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]pyridin-4(1H)-one
Reaction equation
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[NH4+:20]>C(O)C>[OH:1][CH2:2][C:3]1[NH:20][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-(Hydroxymethyl)-5-[(4-methoxybenzyl)oxy]-4H-pyran-4-one (1.2 g, 4.56 mmol) was dissolved in ethanol (3.0 mL), added an aqueous solution of ammonium (9.0 mL), sealed, and stirred at 100° C. for 6 hours. This operation was conducted for 4 lots, and the following treatments were conducted as a whole. The reaction solution was concentrated in vacuo. After adding diethylether, the reaction solution was cooled with ice. The deposited solid was filtered, washed with diethylether, and concentrated in vacuo. The title compound (4.0 g (yield 84%)) was obtained as a brown powder crystal.
Workup
- customsealed
- concentrationThe reaction solution was concentrated in vacuo
- additionAfter adding diethylether
- temperaturethe reaction solution was cooled with ice
- filtrationThe deposited solid was filtered
- washwashed with diethylether
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bf46d2f0fcf241da9a210acedbd996c0
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08551985B2
Reaction notes
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