Ethyl 2-(3-nitrophenoxy)tetradecanoate → 2-(m-Aminophenoxy)-myristic acid ethyl ester

HRID 620698Notes

Reaction equation

HRID 620698 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:2].[H][H]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:2]

Participants

5

Reactant 2

HCID 14122414Ethyl 2-(3-nitrophenoxy)tetradecanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 141224152-(m-Aminophenoxy)-myristic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 154 g (0.39 mol) of 2-(m-nitrophenoxy)-myristic acid ethyl ester in 500 ml of ethanol is placed in an autoclave. An amount of 8 ml of Raney nickel is added. Reduction of the nitro group is carried out with hydrogen gas at an initial pressure of 10-10.5 MPa and a temperature of 65° C. After the reduction (2 h) the solvent is removed by evaporation.

Workup

  1. customa temperature of 65° C
  2. customAfter the reduction (2 h) the solvent is removed by evaporation

Sources & evidence

ORD record
ord-55fd5ee8d23f4e25b616d18e1d65be2f
Source dataset
uspto-grants-1989_04
Patent number
US04822729

Reaction notes

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