Toluene → 3,5-Diamino-4-chlorobenzonitrile

HRID 261903Notes

Reaction equation

HRID 261903 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:13]([O-])=O.P(Cl)(Cl)(Cl)=O.C1(C)C=CC=CC=1>[Fe].C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:9]([NH2:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH2:13]

Participants

6

Reactant 3

HCID 1140TolueneHCID 160084-Chloro-3,5-dinitrobenzonitrileHCID 24813Phosphorus oxychloride

Product 1

HCID 124029953,5-Diamino-4-chlorobenzonitrileYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22272177Toluene waterSolvent

Procedure

By reaction with ammonia at about 0° C. to about 20° C., 4-chloro-3,5-dinitrobenzoic acid amide is obtained which is converted into 4-chloro-3,5-dinitrobenzonitrile by reaction with phosphorus oxychloride in boiling toluene. By reduction in boiling toluene/water with iron, 4-chloro-3,5-diaminobenzonitrile (melting point about 172° C.) is obtained in about 80% yield.

Sources & evidence

ORD record
ord-cec76e1ecaf146878ef768680f26cebf
Source dataset
uspto-grants-1979_05
Patent number
US04152510

Reaction notes

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