2-((5-Methoxy-2-nitrophenyl)amino)ethanol → N-(2-hydroxyethyl)-5-methoxy-2-aminoaniline

HRID 624056Notes

Reaction equation

HRID 624056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-])=O)=[C:7]([NH:9][CH2:10][CH2:11][OH:12])[CH:8]=1>[Pd].CCO>[NH2:13][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=1[NH:9][CH2:10][CH2:11][OH:12]

Participants

4

Reactant 1

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

Product 1

HCID 68830082N-(2-hydroxyethyl)-5-methoxy-2-aminoaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask, 2-((5-methoxy-2-nitrophenyl)amino)ethanol (1.43 g, 6.74 mmol), Pd/C (150 mg) and EtOH (30 mL, degassed) was added. The flask was evacuated and backfilled with H2 and the reaction mixture was stirred under H2-atmosphere at rt for 18 h. The reaction mixture was filtered over celite, washed with MeOH and the solvent was removed under reduced pressure to yield 2-((2-amino-5-methoxyphenyl)amino)ethanol as a red solid which was used as such without further purification. LC-MS conditions B: tR=0.30 min, [M+H]+=183.25.

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction mixture was filtered over celite
  3. washwashed with MeOH
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-27b4b423f68741ae8a5e39654c5e41f5
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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