Diethyl Ether → 3-(2-Aminoethoxy)benzenamine

HRID 596601Notes

Reaction equation

HRID 596601 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7]([NH2:9])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[H-]>O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH2:7][NH2:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 166653HydrideHCID 104872522-(3-Aminophenoxy)acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 214503233-(2-Aminoethoxy)benzenamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-aminophenoxyacetamide (10.0 g., 0.05 M), lithium aluminum hydride (6.8 g., 0.18 M) and ether (250 ml.) is refluxed under dry nitrogen for four days. It is then cooled to room temperature and water slowly added to decompose unreacted hydride. The precipitated salts are removed by filtration and the filtrate concentrated to an oil under reduced pressure. The crude oil is chromatographed on silica gel using 20% methanol/ethyl acetate as eluting agent. Concentration of appropriate fractions affords 4.83 g. (53%) of product as an oil. It is used without further purification.

Workup

  1. temperatureis refluxed under dry nitrogen for four days
  2. customThe precipitated salts are removed by filtration
  3. concentrationthe filtrate concentrated to an oil under reduced pressure
  4. customThe crude oil is chromatographed on silica gel using 20% methanol/ethyl acetate
  5. washas eluting agent
  6. customConcentration of appropriate fractions affords 4.83 g
  7. customIt is used without further purification

Sources & evidence

ORD record
ord-ead4700b453b4c2db658b97fa9a81603
Source dataset
uspto-grants-1977_03
Patent number
US04011324

Reaction notes

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