Nitrogen → 4-(2-((2-Methoxyethoxy)methoxy)ethoxy)aniline

HRID 2274294Notes

Reaction equation

HRID 2274294 reaction equation
N#N.[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1>CO.[Pd]>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 902338741-(2-((2-Methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene

Product 1

HCID 867243654-(2-((2-Methoxyethoxy)methoxy)ethoxy)anilineYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

In a 50 mL 3-neck RBF equipped with N2 Bubbler and gas purger; to a suspension of Pd—C (1.0 g) in methanol (10 mL) was added 1-(2-((2-methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene (5.0 g) in methanol (20 mL) under nitrogen atmosphere. Hydrogen gas was bubbled through the reaction mixture for 2 h at room temperature. The reaction was monitored on TLC using ethyl acetate:hexane (5:5) as mobile phase. After completion of the reaction, the reaction mixture was filtered using Celite and washed with methanol. The filtrate was concentrated under reduced pressure at 40° C. to give 4.28 g of 4-(2-((2-methoxyethoxy)methoxy)ethoxy)aniline as a brown liquid.

Workup

  1. customHydrogen gas was bubbled through the reaction mixture for 2 h at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-2ae7a6d6deb74288b4b64977e43bc6b3
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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