3,4-Dichloroaniline → 2-(3,4-Dichloro-phenylamino)-propionic Acid

HRID 1870301Notes

Reaction equation

HRID 1870301 reaction equation
ClC1C=C(C=CC=1Cl)N.C(OCC)(=O)C(C)=O.C([O:20][C:21](=[O:33])[CH:22]([CH3:32])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)C>>[Cl:31][C:26]1[CH:25]=[C:24]([NH:23][CH:22]([C:21]([OH:33])=[O:20])[CH3:32])[CH:29]=[CH:28][C:27]=1[Cl:30]

Participants

4

Reactant 3

HCID 72573,4-DichloroanilineHCID 12041Ethyl pyruvateHCID 69148082-(3,4-Dichloro-phenylamino)-propionic Acid ethyl ester

Product 1

HCID 69164262-(3,4-Dichloro-phenylamino)-propionic Acid

Procedure

Alternatively, following General Procedure A above and using 3,4-dichloroaniline (Aldrich) and ethyl pyruvate (Aldrich), N-(3,4-dichlorophenyl)-D,L-alanine ethyl ester was prepared as an oil. The reaction was monitored by tlc on silica gel (Rf=0.4 in 25% EtOAc/Hexanes) and purification was by preparative plate chromatography (silica gel using 25% EtOAc/Hexanes as eluent).

Workup

  1. customwas prepared as an oil
  2. customThe reaction was monitored by tlc on silica gel (Rf=0.4 in 25% EtOAc/Hexanes) and purification

Sources & evidence

ORD record
ord-31f09790a74e4635941fe74f1e3574e8
Source dataset
uspto-grants-2000_08
Patent number
US06096782

Reaction notes

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