Isopropanol → 2,5-Diamino-4-chlorotoluene

HRID 2249029Notes

Reaction equation

HRID 2249029 reaction equation
C(O)(C)C.[Cl:5][C:6]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([CH3:16])=[CH:9][C:7]=1[NH2:8].[OH-].[K+]>C1(=O)C=CC=CC1=O.O>[Cl:5][C:6]1[CH:12]=[C:11]([NH2:13])[C:10]([CH3:16])=[CH:9][C:7]=1[NH2:8]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 199955122-Chloro-5-methyl-4-nitroaniline

Product 1

HCID 791932,5-Diamino-4-chlorotolueneYield 91.4%

Reagents, catalysts & solvents 2

HCID 114211,2-BenzoquinoneCatalystHCID 962WaterSolvent

Procedure

A reaction vessel was charged with 60 g of isopropyl alcohol, 50 g of water, 37.3 g of 2-chloro-5-methyl-p-nitroaniline, 5 g of potassium hydroxide and 0.6 g of 1,2-benzoquinone, and then the same procedure as in Example 1 was followed, to obtain 28.6 g of 2-chloro-5-methyl-p-phenylenediamine.

Sources & evidence

ORD record
ord-c43e1bca86e541418a193be20c01b78a
Source dataset
uspto-grants-1991_08
Patent number
US05041672

Reaction notes

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