Acetaminophen → HCID 17755421, compound

HRID 1294067Notes

Reaction equation

HRID 1294067 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[C:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([O:22][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:12](=[O:14])[CH3:13])=[CH:21][CH:20]=2)=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 17755421HCID 17755421, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-chloro-3-nitropyridine (2.77 g, 16.0 mmol) in DMF (55 mL) was added 4-acetylaminophenol (2.67 g, 17.5 mmol) followed by K2CO3 (3.3 g, 5.0 mmol) and stirred at room temperature for 2 hrs. The solvent was removed by evaporation. To the residue, water was added to form a precipitate. The solid was collected by filtration, washed with water and ethyl acetate then dried under reduced pressure to give the title compound (4.32 g, 94%): MS m/e 289 (M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. additionTo the residue, water was added
  3. customto form a precipitate
  4. filtrationThe solid was collected by filtration
  5. washwashed with water and ethyl acetate
  6. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-45e84c693b0d4222bfcb220e4373de83
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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