5-Nitrosalicylic acid → 4,4'-Diaminodiphenyl Ether

HRID 1071902Notes

Reaction equation

HRID 1071902 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)C(O)=O.O[C:15]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:16]=1C(O)=O.ClC1C=CC([N+]([O-])=O)=CC=1.[OH-].[Na+]>[C].[Pd]>[CH:20]1[C:21]([NH2:24])=[CH:22][CH:23]=[C:15]([O:1][C:2]2[CH:10]=[CH:6][C:5]([NH2:11])=[CH:4][CH:3]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 73185-Nitrosalicylic acidHCID 74741-Chloro-4-nitrobenzeneHCID 118825-Hydroxy-2-nitrobenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 75794,4'-Diaminodiphenyl Ether

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A 5-hydroxy-2-nitrobenzoic acid derivative (e.g. sodium 5-hydroxy-2-nitrobenzoate) or a 2-hydroxy-5-nitrobenzoic acid derivative (e.g. sodium 2-hydroxy-5-nitrobenzoate) is reacted with 4-chloronitrobenzene in the presence of an alkali (e.g. sodium hydroxide), followed by hydrogenation using palladium-carbon, to give the corresponding 4,4′-diaminodiphenyl ether 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-9841806aa8d84c6f9d9f143a8b379066
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Reaction notes

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