Acetaminophen → N-acetyl-4-(pyrid-2-ylmethoxy)aniline

HRID 1975736Notes

Reaction equation

HRID 1975736 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 19098335N-acetyl-4-(pyrid-2-ylmethoxy)aniline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-acetamidophenol (120 g; 796 mmol), 2-picolyl chloride hydrochloride (130.6 g; 796 mmol), and powdered potassium carbonate (330 g; 2.39 mol) in 1500 mL DMF was stirred at ambient temperature for 7 days. The reaction was poured into brine and the precipitate was collected by vacuum filtration. The solids were washed with water followed by diethyl ether. The reaction yielded N-acetyl-4-(pyrid-2-ylmethoxy)aniline as a beige solid.

Workup

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washThe solids were washed with water

Sources & evidence

ORD record
ord-224274fc302a46e38bec89cd50e40e03
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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