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

HRID 639034Notes

Reaction equation

HRID 639034 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>[C:20]([O:1][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:7](=[O:9])[CH:8]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 151595322-(Hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]pyridin-4(1H)-one

Product 1

HCID 66598536[5-[(4-methoxyphenyl)methoxy]-4-oxo-1H-pyridin-2-yl]methyl acetateYield 51.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(hydroxymethyl)-5-({[4-(methoxy)phenyl]methyl}oxy)-4(1H)-pyridinone (26 g, 0.1 mol) in pyridine (150 mL) was cooled to 5° C. and treated with acetyl chloride (10.48 ml, 0.149 mol). The reaction mixture was stirred and allowed to warm to room temperature then heated at 60° C. for 18 hours. Pyridine was evaporated under vacuum and the residue was triturated with water (250 mL), cooled in an ice-bath for 30 minutes. The solid formed was filtered off, washed with cold water and dried in vacuo to afford the product as a solid (15.7 g, 50%); MS (+ve ion electrospray) m/z 304 (MH+).

Workup

  1. temperaturethen heated at 60° C. for 18 hours
  2. customPyridine was evaporated under vacuum
  3. customthe residue was triturated with water (250 mL)
  4. temperaturecooled in an ice-bath for 30 minutes
  5. customThe solid formed
  6. filtrationwas filtered off
  7. washwashed with cold water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0b00a3e2d66544d280a4f0a6c186477e
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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