Sulfuric Acid → Benzidine

HRID 1071900

Reaction equation

HRID 1071900 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1C(O)=O)([O-])=O.[N+](C1C=C(C=CC=1)C(O)=O)([O-])=O.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O-])=O.[OH-].[Na+].N(C1C=CC=CC=1)NC1C=CC=CC=1.S(=O)(=O)(O)O>[Zn]>[NH2:25][C:28]1[CH:33]=[CH:32][C:31]([C:10]2[CH:11]=[CH:12][C:4]([NH2:1])=[CH:5][CH:9]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 84973-Nitrobenzoic acidHCID 110872-Nitrobenzoic acidHCID 14798Sodium HydroxideHCID 31222Hydrazobenzene

Product 1

HCID 7111Benzidine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A 2-nitrobenzoic acid derivative (e.g. sodium 2-nitrobenzoate) or a 3-nitrobenzoic acid derivative (e.g. sodium 3-nitrobenzoate) and nitrobenzene are treated with zinc dust in the presence of an alkali (e.g. sodium hydroxide) and the resulting hydrazobenzene derivative is treated with sulfuric acid, to give the corresponding 4,4′-diaminobiphenyl derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Sources & evidence

ORD record
ord-584fb01b4f5e42328545d2572c0559c7
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Linked notes

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