Hydrochloric Acid → 2-Amino-5-bromobenzonitrile

Reaction equation

BrC1C=CC([N+]([O-])=O)=C(C=1)N.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-])=O)=[C:17]([CH:20]=1)[C:18]#[N:19].NC1C=CC=CC=1.N([O-])=O.[Na+].Cl>>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:21])=[C:17]([C:18]#[N:19])[CH:20]=1

Participants

Reactant 5

HCID 313Hydrochloric Acid2×

HCID 6115Aniline

HCID 3194895-Bromo-2-nitrobenzonitrile

HCID 53147665-Bromo-2-nitroaniline

HCID 23668193Sodium Nitrite

Product 1

HCID 4297402-Amino-5-bromobenzonitrile

Procedure

5-bromo-2-nitroaniline is converted into 5-bromo-2-nitrobenzonitrile by treating the aniline derivative with sodium nitrite and hydrochloric acid and reacting the resulting diazonium salt with cuprous cyanide as in Example 2. The nitro group is reduced with stannous chloride and hydrochloric acid to give 4-bromo-2-cyanoaniline.