Aniline → HCID 18506458, compound

HRID 1355313Notes

Reaction equation

[N+:1]([C:4]1[C:5](=O)[C:6]2[C:14](=[CH:15][CH:16]=1)[C:13]1[C:8](=[CH:9][C:10]([N+:17]([O-:19])=[O:18])=[CH:11][CH:12]=1)[CH:7]=2)([O-:3])=[O:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([N+:17]([O-:19])=[O:18])=[CH:11][CH:12]=3)[C:7]([C:16]3[CH:15]=[CH:14][CH:6]=[CH:5][C:4]=3[NH2:1])([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[NH2:21])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 6115Aniline

HCID 86586492HCID 86586492, compound

Product 1

HCID 18506458HCID 18506458, compound

Procedure

2,7-Bis(diarylamino)-9,9-bis(diarylaminophenyl)fluorene, a compound of this invention, can be synthesized according to the above synthetic route as follows: A mixture of a 2,7-dinitrofluorenone and an aniline is refluxed in the presence of an acid catalyst to give an intermediate 2,7-dinitro-9,9-bis(aminophenyl)fluorene. The two nitro groups are then converted to two amino groups by a reduction reaction with Fe/NH4Cl. Finally, the reduced intermediate is reacted with aryl halides (Ar—X and Ar′—X, stepwise) in the presence of a catalyst such as palladium to produce the desired product.

Sources & evidence

ORD record: ord-aa6fb3778b194444a6b9f765d871518c
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586120B2

Reaction notes

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