1-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene → 4-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)aniline

HRID 78706Notes

Reaction equation

HRID 78706 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 146918221-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene

Product 1

HCID 219176404-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 17 (1.39 g, 4.86 mmol) in acidic EtOH (5 mL) in a Parr apparatus was added a catalytic amount of 20% Pd/C (0.05 g). The reaction vessel was purged with H2 then pressurized to 70 psi. After stirring for 16 h the reaction mixture was filtered through a 4 cm pad of celite and concentrated under reduced pressure to afford 18 as a brown oil (1.24 g, 100%): 1H NMR (300 MHz, CDCl3) δ 6.75 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.8 Hz, 2H), 4.11-3.99 (m, 2H), 3.87-3.78 (m, 2H), 3.76-3.51 (m, 8H), 3.42 (s, 1H), 3.38 (s, 2H).

Workup

  1. customThe reaction vessel was purged with H2
  2. filtrationwas filtered through a 4 cm pad of celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23385a405c43460ca4f6669e15013861
Source dataset
uspto-grants-2014_09
Patent number
US08841460B2

Reaction notes

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