Ethanolamine → 2-((5-Methoxy-2-nitrophenyl)amino)ethanol

HRID 624055Notes

Reaction equation

HRID 624055 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([CH2:15][NH2:16])[OH:14]>O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:16][CH2:15][CH2:13][OH:14])[CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 129667452-Bromo-4-methoxy-1-nitrobenzene

Product 1

HCID 1496062-((5-Methoxy-2-nitrophenyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A round bottom flask was charged with 2-bromo-4-methoxy-1-nitrobenzene (2.0 g, 8.6 mmol) and ethanolamine (8.1 mL, 135 mmol). The resulting reaction mixture was stirred at 50° C. for 4 h and at rt for 48 h, then water (32.0 mL) was added and the resulting precipitate was filtered off and rinsed with water to yield 2-((5-methoxy-2-nitrophenyl)amino)ethanol as a yellow solid LC-MS conditions B: tR=0.56 min, [M+H]+=213.13.

Workup

  1. customThe resulting reaction mixture
  2. filtrationthe resulting precipitate was filtered off
  3. washrinsed with water

Sources & evidence

ORD record
ord-37c7380dbf394627a2c2a0ca660b4beb
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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