1-(1-Methylethoxy)-2-nitrobenzene → 2-(1-Methylethoxy)benzenamine

HRID 1110428Notes

Reaction equation

HRID 1110428 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O)[CH3:3].[H][H]>CO.[Ni]>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:1]

Participants

5

Reactant 2

HCID 1971801-(1-Methylethoxy)-2-nitrobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 344362-(1-Methylethoxy)benzenamineYield 94.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-(1-methylethoxy)-2-nitrobenzene, 45.26 g (0.25 mol) is dissolved in 500 ml of methanol, 4 g Raney nickel is added and the mixture is 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 35.7 g (94.4%) of 2-(1-methylethoxy)benzenamine; bp 100-102 (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-e14674bd76dd44d3a7e659f0c645e421
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

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