1-(Hexyloxy)-2-nitrobenzene → 2-(Hexyloxy)aniline

HRID 1110429Notes

Reaction equation

HRID 1110429 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H]>CO.[Ni]>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 150681131-(Hexyloxy)-2-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 159374522-(Hexyloxy)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(Hexyloxy)-2-nitrobenzene, 61.28 g (0.27 mol) is dissolved in 700 ml of methanol, 3 g Raney nickel is added and the mixture exposed to hydrogen gas until the required amount of hydrogen is absorbed. The methanol solution is filtered and concentrated in vacuo and the residue distilled to give 50 g of 2-(hexyloxy)benzenamine; bp 145°-148° C. at 4 mm.

Workup

  1. customis absorbed
  2. filtrationThe methanol solution is filtered
  3. concentrationconcentrated in vacuo
  4. distillationthe residue distilled

Sources & evidence

ORD record
ord-b65654df64f84755832fadaf785add3c
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

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