2-Nitroaniline → 4,4'-Bis-(o-nitroanilino) biphenyl

HRID 262696

Reaktionsgleichung

Reaktionsgleichung von HRID 262696
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N+:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])([O-:17])=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>[N+](C1C=CC=CC=1)([O-])=O>[N+:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 69462-NitroanilineHCID 71104,4'-DibromobiphenylHCID 10340Sodium Carbonate

Produkt 1

HCID 538486924,4'-Bis-(o-nitroanilino) biphenylAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

4,4'-Dibromobiphenyl (156 g., 0.5 mole) was condensed with o-nitroaniline (138 g., 1.0 mole) using cuprous iodide catalyst and anhydrous sodium carbonate as an acid acceptor in refluxing nitrobenzene (500 ml) during 16 hours. The resulting 4,4'-bis-(o-nitroanilino) biphenyl, obtained in 85% yield, was reduced with sodium sulfide in ethylene glycol at 150° to 200° C. The yield of 4,4'-bis(o-aminoanilino)biphenyl was 132 g. (72% yield, mp 211°-222° C.). The melting behavior of the compound is unusual. Differential Scanning Calorimetry (DSC) analysis provides two endotherms; one at 211° C. and one at 222° C. Depending on the thermal history of the amine, either melting point (or combination) is observed. The amine assay by acetylation was 16.2, theory 16.93. The elemental analysis provided the following:

Quellen und Nachweise

ORD-Eintrag
ord-25bdcf4efe034ffc9a28b2a80f13c483
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154919

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