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

HRID 1297057Notes

Reaction equation

HRID 1297057 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 669277274-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}nitrobenzene

Product 1

HCID 669278494-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}anilineYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A portion of 14 (5.77 g, 20.2 mmol) was dissolved in 40 mL of acidic ethanol, and a catalytic amount of 10% palladium on carbon was added. The mixture was hydrogenated on a Parr apparatus (60 psi, 70° C.) for 3 hours. The mixture was then filtered over Celite, washing with ethanol. Solid sodium bicarbonate was added, and the mixture was stirred for 2 hours and, then filtered. The solvent was removed by distillation at reduced pressure, leaving a brown oil (5.0 g, 98% yield). IR (neat) 3441.82, 3349.64, 2893.88, 2238.41, 1634.41, 1516.36, 1449.79, 1234.71, 1101.56, 906.97, 722.62 cm−1. 1H NMR (400 MHz, CDCl3) δ 6.65 (ABq, J=8.7 Hz, Δv=51.5 Hz, 4H), 4.01 (t, J=5.4 Hz, 2H), 3.77 (t, J=4.6 Hz, 2H), 3.69 (app t, J=5.6 Hz, 2H), 3.65 to 3.59 (m, 4H), 3.51 (app t, J=4.9 Hz, 2H), 3.34 (s, 3H), 3.0 (brs, 2H). 13C NMR (100 MHz, CDCl3) δ 152.30, 140.58, 116.75, 116.24, 72.31, 71.14, 71.02, 70.93, 70.30, 68.49, 59.44.

Workup

  1. filtrationThe mixture was then filtered over Celite
  2. washwashing with ethanol
  3. additionSolid sodium bicarbonate was added
  4. filtrationfiltered
  5. customThe solvent was removed by distillation at reduced pressure

Sources & evidence

ORD record
ord-e355dac7d1eb46a190e867812e7e8af7
Source dataset
uspto-grants-2007_07
Patent number
US07250147B2

Reaction notes

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