(2-Nitrophenyl)acetic acid → 2-(2-(Dimethylamino)ethyl)aniline

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](O)=O)([O-])=O.[CH3:14][N-:15][CH3:16].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:14][N:15]([CH3:16])[CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

Reactant 3

HCID 77337(2-Nitrophenyl)acetic acid

HCID 182180Dimethylazanide

HCID 21226445Aluminium lithium hydride

Product 1

HCID 128169352-(2-(Dimethylamino)ethyl)aniline

Procedure

The title compound was prepared from 2-nitrophenylacetic acid by conversion to the N,N-dimethylamide, hydrogenation then reduction with lithium aluminium hydride.

Sources & evidence

ORD record: ord-e77cd5eb4839456289f6a09aff54c92d
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972937

Reaction notes

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