2-Amino-5-bromobenzonitrile → 3-Amino-5-bromo-1H-indazole

HRID 1283708Notes

Reaction equation

HRID 1283708 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]#[N:10])[CH:3]=1.[N:11]([O-])=O.[Na+]>Cl>[NH2:10][C:9]1[C:4]2[C:5](=[CH:7][CH:8]=[C:2]([Br:1])[CH:3]=2)[NH:6][N:11]=1

Participants

4

Reactant 2

HCID 4297402-Amino-5-bromobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 8179103-Amino-5-bromo-1H-indazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

Twenty grams of 4-bromo-2-cyanoaniline is treated with concentrated hydrochloric acid and sodium nitrite; the resulting diazo compound is reacted with stannous chloride in concentrated hydrochloric acid at 0° C. Working up as in Example 2 gives 3-amino-5-bromoindazole.

Sources & evidence

ORD record
ord-f7e31818a0d440dcb9d8617ebdad3d91
Source dataset
uspto-grants-1976_08
Patent number
USRE028939

Reaction notes

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