5-Hydroxy-2-nitrobenzoic acid → 4,4'-Diaminodiphenyl Ether

HRID 1071896Notes

Reaction equation

HRID 1071896 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:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=1S(O)(=O)=O.ClC1C([N+]([O-])=O)=C(C=CC=1)C(O)=O.ClC1C=CC([N+]([O-])=O)=CC=1C(O)=O.[OH-].[Na+]>[C].[Pd]>[CH:17]1[C:18]([NH2:21])=[CH:19][CH:20]=[C:15]([O:1][C:2]2[CH:10]=[CH:6][C:5]([NH2:11])=[CH:4][CH:3]=2)[CH:16]=1

Participants

7

Reactant 5

HCID 118825-Hydroxy-2-nitrobenzoic acidHCID 14798Sodium HydroxideHCID 172872-Chloro-5-nitrobenzoic acidHCID 209023-Chloro-2-nitrobenzoic acidHCID 692252-Hydroxy-5-nitrobenzenesulphonic acid

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-nitrobenzenesulfonic acid derivative (e.g. sodium 2-hydroxy-5-nitrobenzoate) is reacted with a 5 chloro-2-nitrobenzoic acid derivative or a 2-chloro-5-nitrobenzoic acid derivative 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-0abdd3727e3f49e2a53f45e13683e264
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Reaction notes

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