Benzoyl chloride → 2-(N-benzoylimino)-4,4'-dinitrobiphenyl

HRID 1377006Notes

Reaction equation

HRID 1377006 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:19])[C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C1C=CN=CC=1)C.CN1CCCC1=O>[C:20]([N:19]=[C:6]1[CH2:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[C:7]1[C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 932654,4'-Dinitro(1,1'-biphenyl)-2-amine

Product 1

HCID 867512112-(N-benzoylimino)-4,4'-dinitrobiphenyl

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In the first step, 4,4'-dinitro-2-biphenylamine is reacted with benzoyl chloride in the presence of 4-dimethylamine pyridine in N-methyl-2-pyrrolidinone (NMP) to give 2-(N-benzoylimino)-4,4'-dinitrobiphenyl. The hydrogenation of the latter in N,N-dimethylacetamide (DMAc) at room temperature with 10% Pd/C as a catalyst provides the desired 2-(N-benzoylimino)-4,4'-diaminobiphenyl.

Sources & evidence

ORD record
ord-971ffbe07f6544068395fb7fd26401a4
Source dataset
uspto-grants-1997_09
Patent number
US05663437

Reaction notes

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