4-Methyl-1-nitro-2-[2-(2-nitrophenoxy)ethoxy]benzene → 2-[2-(2-Aminophenoxy)ethoxy]-4-methylaniline

HRID 1852366Notes

Reaction equation

HRID 1852366 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH:3]=1>[Pd].O1CCOCC1>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH2:12][O:11][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[NH2:8]

Participants

4

Reactant 1

HCID 27630554-Methyl-1-nitro-2-[2-(2-nitrophenoxy)ethoxy]benzene

Product 1

HCID 136852532-[2-(2-Aminophenoxy)ethoxy]-4-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

100 g 4-methyl-1-nitro-2-(2-(2-nitro-phenoxy)-ethoxy)-benzene and 10 g palladium on charcoal were suspended in 3.5 l dioxane and hydrogenated at room temperature under a hydrogen pressure of 5.5 bar. After flashing three times with nitrogen the catalyst was filtered off under a nitrogen atmosphere and the remaining solution was evaporated and the product was dried under vacuum. Yield: 80 g.

Workup

  1. filtrationwas filtered off under a nitrogen atmosphere
  2. customthe remaining solution was evaporated
  3. customthe product was dried under vacuum

Sources & evidence

ORD record
ord-8649fc206d834f878209c93193575a1d
Source dataset
uspto-grants-2015_02
Patent number
US08962338B2

Reaction notes

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