Toluene → 2,5-Diamino-4-chlorotoluene

HRID 2249028Notes

Reaction equation

HRID 2249028 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[C:10]([N+:17]([O-])=O)=[CH:11][C:12]([CH3:16])=[C:13]([CH:15]=1)[NH2:14].[OH-].[Na+]>C1(O)C2C(=CC=CC=2)C(O)=CC=1.O>[Cl:8][C:9]1[CH:15]=[C:13]([NH2:14])[C:12]([CH3:16])=[CH:11][C:10]=1[NH2:17]

Participants

6

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 837726-Chloro-4-nitro-o-toluidine

Product 1

HCID 791932,5-Diamino-4-chlorotolueneYield 94%

Reagents, catalysts & solvents 2

HCID 113051,4-NaphthalenediolCatalystHCID 962WaterSolvent

Procedure

A reaction vessel was charged with 60 g of toluene, 50 g of water, 37.3 g of 5-chloro-2-methyl-p-nitroaniline, 6 g of sodium hydroxide and 0.3 g of 1,4-naphthalenediol, and then the same procedure as in Example 1 was followed, to obtain 29.4 g of 2-chloro-5-methyl-p-phenylenediamine.

Sources & evidence

ORD record
ord-7556cd264c83430585909fcb1698f416
Source dataset
uspto-grants-1991_08
Patent number
US05041672

Reaction notes

Loading…