2-Aminophenol → 2-(Isopropylamino)phenol

HRID 1782549Notes

Reaction equation

HRID 1782549 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].CN(C)C=O.I[CH:15]([CH3:17])[CH3:16]>C(=O)([O-])O.[K+].O>[CH:15]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 58012-AminophenolHCID 6228DimethylformamideHCID 6362Isopropyl iodide

Product 1

HCID 5860122-(Isopropylamino)phenol

Reagents, catalysts & solvents 2

HCID 516893Potassium BicarbonateCatalystHCID 962WaterSolvent

Procedure

Into a 100 mL flask purged with nitrogen were added 12 g (109.92 mmol) of o-aminophenol and 60 mL of dimethylformamide (DMF), and the resultant mixture was stirred at room temperature and dissolved. Then, the obtained solution was mixed with 22.4 g (132 mmol) of 2-iodopropane such (molar ratio of 2-iodopropane to o-aminophenol: 1.2), and further with 11.4 g (114 mmol) of potassium hydrogencarbonate (KHCO3) as a catalyst, and the resultant mixture was stirred at room temperature for 5 h. After conducting the reaction for 5 h, 50 mL of water was added to the reaction solution to terminate the reaction.

Workup

  1. customInto a 100 mL flask purged with nitrogen
  2. dissolutiondissolved
  3. customthe reaction for 5 h
  4. customto terminate
  5. customthe reaction

Sources & evidence

ORD record
ord-25599238006d4dc4b25790d8a0361922
Source dataset
uspto-grants-2009_03
Patent number
US07498467B2

Reaction notes

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