4-Aminophenol → 4-[(3-Nitropyridin-2-yl)amino]phenol

HRID 976119Notes

Reaction equation

HRID 976119 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([OH:18])[CH:12]=1>CN(C)C=O>[N+:8]([C:7]1[C:2]([NH:17][C:16]2[CH:11]=[CH:12][C:13]([OH:18])=[CH:14][CH:15]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 151750814-[(3-Nitropyridin-2-yl)amino]phenolYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8.17 g (50 mmol) of 2-chloro-3-nitropyridine and 16.70 g (150 mmol) of p-aminophenol were added to 50 ml of dimethylformamide and the mixture was stirred at 100° C. for 40 min. The solvent was distilled off under reduced pressure, the same treatment as that of Production Example 1 was repeated and the product was recrystallized from ethanol to obtain 9.4 g of the title compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-7a3e99ad49c04420a0c777a48c888724
Source dataset
uspto-grants-1997_03
Patent number
US05610304

Reaction notes

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