Hydrochloric Acid → Nitrobenzene

HRID 703343Notes

Reaction equation

HRID 703343 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)CCl)([O-:3])=[O:2].Cl.[OH-].[K+].[H-].[Na+]>CN(C)P(N(C)C)(N(C)C)=O.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12078alpha-Chloro-m-nitrotolueneHCID 14797Potassium HydroxideHCID 24758Sodium hydride

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A derivative of 3-nitrobenzyl chloride (IV) and a compound of the formula (V) are reacted in a solvent such as dimethylformamide, hexamethylphosphoramide, etc., in the presence of a hydrogen chloride acceptor such as KOH, NaH, etc., at a temperature in the range from -10° to 150° C., preferably from 0° to 80° C., for 0.1 to 20 hours, preferably 0.5 to 10 hours, to obtain a nitrobenzene derivative of the formula (VI). This nitrobenzene derivative is reduced into an aniline derivative (VII) by a conventional method, for example, by adding hydrazine hydrate to said nitrobenzene derivative in an alcohol and heating the solution under reflux in the presence of palladium-charcoal for 1 to 10 hours.

Sources & evidence

ORD record
ord-a342a50516074b9c894e512fb4a9fdf0
Source dataset
uspto-grants-1991_01
Patent number
US04983209

Reaction notes

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