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

HRID 2366085Notes

Reaction equation

HRID 2366085 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.Cl[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 19098335N-acetyl-4-(pyrid-2-ylmethoxy)anilineYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-acetamidophenol (Sigma-Aldrich; 73.6 g), 2-chloromethylpyridine hydrochloride (80 g) and cesium carbonate (320 g) in DMF (1 L) was stirred at 70° C. for 2 days. The mixture was cooled, poured into water (2 L) and extracted with EtOAC (×6). The organic layers were washed with brine, dried (MgSO4) and filtered to give a tan solid (114 g) which was used as such in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAC (×6)
  3. washThe organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-65989a8012bb476e82189ab670ca11e5
Source dataset
uspto-grants-2014_04
Patent number
US08697730B2

Reaction notes

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