1-chloro-2,4-dimethoxy-3,5-dinitrobenzene → HCID 18779321, compound

HRID 1607473Notes

Reaction equation

HRID 1607473 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([O:12][CH3:13])[C:6]([N+:14]([O-])=O)=[CH:5][C:4]=1[Cl:17]>[Fe].C(O)(=O)C>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[C:7]([O:12][CH3:13])[C:6]([NH2:14])=[CH:5][C:4]=1[Cl:17]

Participants

4

Reactant 1

HCID 2849581-chloro-2,4-dimethoxy-3,5-dinitrobenzene

Product 1

HCID 18779321HCID 18779321, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

2,4-Dimethoxy-3,5-dinitrochlorobenzene is reduced with iron in the presence of acetic acid, at a temperature of between 50° and 100° C. 2,4-Dimethoxy-3,5-diaminochlorobenzene is thereby obtained, and this is then subjected to a dehalogenation reaction. This reaction is performed in water, in a lower alcohol or in an aqueous-alcoholic mixture, in the presence of palladium on charcoal, ammonium acetate and triethylamine formate, at a temperature between 50° C. and the refluxing temperature of the solvent.

Sources & evidence

ORD record
ord-af38133715bc42e7b3eab9855249e0e4
Source dataset
uspto-grants-1989_09
Patent number
US04865619

Reaction notes

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