1-(2-Methoxyethoxy)-4-nitrobenzene → 4-(2-Methoxyethoxy)aniline

HRID 1812098Notes

Reaction equation

HRID 1812098 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 5478091-(2-Methoxyethoxy)-4-nitrobenzene

Product 1

HCID 38798854-(2-Methoxyethoxy)anilineYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2-methoxyethoxy)-4-nitrobenzene (0.724 g, 3.67 mmol) and 10% Pd/C (Aldrich) (0.201 g, 1.89 mmol) in EtOH (10 mL) was evacuated under vacuum and refilled with hydrogen (4 times). The mixture was hydrogenated under balloon pressure at rt for 1.5 h. The reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH) and concentrated. The crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%) to give 4-(2-methoxyethoxy)aniline (0.548 g, 89% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 6.73-6.82 (m, 2H); 6.58-6.68 (m, 2H); 4.01-4.08 (m, 2H); 3.67-3.76 (m, 2H); 3.29-3.52 (m, 5H). m/z (ESI, +ve ion) 168.1 (M+H)+.

Workup

  1. customwas evacuated under vacuum
  2. additionrefilled with hydrogen (4 times)
  3. filtrationThe reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH)
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%)

Sources & evidence

ORD record
ord-1014bdbd1b734ba3bad3ae80323c48ca
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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