Acetaminophen → Acetamide, N-[4-(2-quinolinylmethoxy)phenyl]-

HRID 1769341Notes

Reaction equation

HRID 1769341 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 2747568Acetamide, N-[4-(2-quinolinylmethoxy)phenyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 2-(chloromethyl)quinoline hydrochloride (100.0 g), 4-acetamidophenol (70.69 g) and milled anhydrous potassium carbonate (194 g) was stirred in DMF (1.2L) using a mechanical stirrer for 48 hours. The mixture was carefully poured onto ice/water (3L) with vigourous stirring. After the ice had melted, the solid was filtered and rinsed thoroughly with water. It was recrystallized from 95% ethanol and filtered to give the title compound in three crops.

Workup

  1. customfor 48 hours
  2. filtrationthe solid was filtered
  3. washrinsed thoroughly with water
  4. customIt was recrystallized from 95% ethanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b874ab2d4af0410fa40d9fce84901840
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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