Acetyl chloride → HCID 57815353, compound

HRID 385583Notes

Reaction equation

HRID 385583 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([O:10][CH3:11])[C:7](=[O:9])[CH:8]=1.[C:12](Cl)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:1][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([O:10][CH3:11])[C:7](=[O:9])[CH:8]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2344112-(Hydroxymethyl)-5-methoxypyridin-4(1H)-one

Product 1

HCID 57815353HCID 57815353, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 8.3 g of 2-(hydroxymethyl)-5-methoxypyridin-4(1H)-one in 30 mL of pyridine, 5.7 mL of acetyl chloride was dropped under cooling with ice. After warming to room temperature, the mixture was stirred at 55 to 60° C. for 2 hours 30 minutes. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=95:1 to 80:20 to obtain 6.7 g of (5-methoxy-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate as a brown foam.

Workup

  1. additionwas dropped
  2. temperatureunder cooling with ice
  3. temperatureAfter cooling to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe resultant residue was purified by flash silica gel column chromatography
  6. washelution with chloroform

Sources & evidence

ORD record
ord-a4130558e6bb4d33837007fd84ef5414
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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