Aniline → Ethyl oxanilate

HRID 1388089Notes

Reaction equation

HRID 1388089 reaction equation
[C:1]([O-:12])(=[O:11])[C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:13]([N+](CC)(CC)CC)[CH3:14].NC1C=CC=CC=1.C(OC(=O)C(OCC)=O)C>[Pt]>[CH2:13]([O:11][C:1](=[O:12])[C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3])[CH3:14]

Participants

5

Reactant 3

HCID 6115AnilineHCID 7268Diethyl OxalateHCID 86739203Tetraethylammonium oxanilate

Product 1

HCID 73826Ethyl oxanilateYield 90%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

The electrochemical oxidation of tetraethylammonium oxanilate was carried out in an one-compartment cell (graphite anode, platinum cathode). The starting material was prepared by firstly reacting aniline and diethyloxalate to give ethyloxanilate which compound was then saponified with tetraethylammonium hydroxide; the yield was more than 90%.

Sources & evidence

ORD record
ord-59aaa2d331ed4a1a900e47dc8acd1d08
Source dataset
uspto-grants-1984_02
Patent number
US04430262

Reaction notes

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