Acetyl chloride → [5-[(4-methoxyphenyl)methoxy]-4-oxo-1H-pyridin-2-yl]methyl acetate

HRID 1038603Notes

Reaction equation

[OH:1][CH2:2][C:3]1[NH:4][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.[C:20](Cl)(=[O:22])[CH3:21]>N1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:6]2[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][O:1][C:20](=[O:22])[CH3:21])[NH:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-(Hydroxymethyl)-5-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one (3.21 g, 12.2 mmol) was dissolved in pyridine (60 mL), added acetyl chloride (1.44 g, 18.3 mmol) under ice-cold conditions, and the mixture was stirred at 60° C. overnight. Then, the reaction solution was concentrated in vacuo. Water was added under ice-cold conditions, and stirred at room temperature for 30 minutes. The deposited solid was filtered, washed with iced water and diethyl ether, concentrated in vacuo, and the title compound (3.56 g (yield 96%)) was obtained as brown powder crystal.

Workup

concentrationThen, the reaction solution was concentrated in vacuo
additionWater was added under ice-cold conditions
stirringstirred at room temperature for 30 minutes
filtrationThe deposited solid was filtered
washwashed with iced water and diethyl ether
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c2b678227db4272aae932053dd3f0e8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

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