2,6-Dimethylnitrobenzene → 2,4,6-Trimethylaniline

HRID 1980461Notes

Reaction equation

HRID 1980461 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-])=O.[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=1N>[Ni]>[CH3:12][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH2:9])=[C:4]([CH3:8])[CH:5]=1.[C:18]1([CH3:1])[CH:19]=[C:13]([CH3:12])[CH:14]=[C:16]([CH3:20])[CH:17]=1

Participants

5

Reactant 2

HCID 66722,6-DimethylnitrobenzeneHCID 68962,6-Dimethylaniline

Product 2

HCID 69132,4,6-TrimethylanilineHCID 7947Mesitylene

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The 2,6-dimethylnitrobenzene is reduced to the amine, i.e., 2,6-dimethylaniline in the presence of a Raney nickel catalyst at a temperature of 25° C. and a pressure of 70 atmospheres: ##STR5## Mesidine (2,4,6-trimethylaniline) can be obtained in a similar manner by nitration of mesitylene followed by reduction. The aromatic amine is then reduced to an aliphatic amine with hydrogen in the presence of a hydrogenation catalyst such as Rh/Al2O3 in the range of 150 atmospheres and a temperature range of 90°-100° C., thusly: ##STR6## The thus formed 2,6-dimethylcyclohexylamine is then phosgenated to 2,6-dimethylcyclohexylisocyanate in the presence of chlorobenzene or dichlorobenzene solvent using excess phosgene and a two-stage temperature reaction wherein the first stage is carried out at -20° to 20° C. and the second from 110° to 180° C. while maintaining the reaction at a pressure in the range of 1 to 15 atmospheres: ##STR7##

Sources & evidence

ORD record
ord-2199a8f513fa43d49e26d8202b1b4ff0
Source dataset
uspto-grants-1985_04
Patent number
US04510097

Reaction notes

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