Potassium Hydroxide → 2,2'-(1,3-Phenylene)bis[1,10-phenanthroline]

HRID 1640351

Reaction equation

HRID 1640351 reaction equation
[NH2:1][C:2]1[C:3]([CH:12]=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=O)[CH3:24])[CH:18]=1)(=O)[CH3:15].[OH-].[K+]>C(O)C>[N:1]1[C:2]2[C:3](=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:12]=[CH:15][C:14]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:24]=[CH:12][C:3]3[C:2](=[C:11]4[C:6](=[CH:5][CH:4]=3)[CH:7]=[CH:8][CH:9]=[N:10]4)[N:1]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 232291,3-DiacetylbenzeneHCID 110520988-Aminoquinoline-7-carboxaldehyde

Product 1

HCID 106704702,2'-(1,3-Phenylene)bis[1,10-phenanthroline]Yield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

101 g of 8-amino-7-quinoline carboaldehyde was reacted with 45 g of 1,3-diacetylbenzene and 100 g of 85% potassium hydroxide in 1800 ml of ethanol for 10 hours while refluxing and a reactant was treated by a normal method to obtain 100 g of 1,3-di(1,10-phenanthroline-2-yl)benzene. 40.8 g of this 1,3-di(1,10-phenanthroline-2-yl)benzene was reacted with 400 ml of phenyl lithium (0.94 M cyclohexane-ether solution) in 750 ml of toluene for 2.5 hours while cooling with ice and a reactant was treated by a normal method. The obtained product was reacted with 118 g of nitrobenzene at 110° C. for 3 hours and a reactant was treated by a normal method to obtain 22.8 g of E-20.

Workup

  1. temperaturewhile refluxing
  2. additiona reactant was treated by a normal method

Sources & evidence

ORD record
ord-ff052704ccb94db2b6875eb26902b4b5
Source dataset
uspto-grants-2012_02
Patent number
US08114529B2

Linked notes

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