Potassium Hydroxide → 2,7-Di(1,10-phenanthroline-2-yl)naphthalene

HRID 1640353

Reaction equation

HRID 1640353 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([C:14](=O)[CH3:15])=[CH:9][CH:10]=2)[CH:5]=1)(=O)[CH3:2].[NH2:17][C:18]1[C:19]([CH:28]=O)=[CH:20][CH:21]=[C:22]2[C:27]=1[N:26]=[CH:25][CH:24]=[CH:23]2.[OH-].[K+]>C(O)C>[N:17]1[C:18]2[C:19](=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[CH:28]=[CH:2][C:1]=1[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([C:14]3[CH:15]=[CH:28][C:19]4[C:18](=[C:27]5[C:22](=[CH:21][CH:20]=4)[CH:23]=[CH:24][CH:25]=[N:26]5)[N:17]=3)=[CH:9][CH:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 110520988-Aminoquinoline-7-carboxaldehydeHCID 156863122,7-Diacetylnaphthalene

Product 1

HCID 576535352,7-Di(1,10-phenanthroline-2-yl)naphthaleneYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

54.0 g of 2,7-dihydroxynaphthalene was dissolved in a mixture of 680 ml of dichloromethane and 136 ml of pyridine, and to this, 228 g of trifluoromethanesulfonic anhydride (produced by TOKYO CHEMICAL INDUSTRY CO., LTD.) was added dropwise at 0° C. After the resulting mixture was reacted at 5° C. for 2 hours and then at room temperature for one day, a reactant was treated by a normal method to obtain 143 g of 2,7-bis(trifluoromethane sulfonyloxy)naphthalene. 143 g of this 2,7-bis(trifluoromethane sulfonyloxy)naphthalene was mixed with 216 ml of n-butyl vinyl ether, 113 ml of triethylamine, 2.78 g of 1,3-bis(diphenylphosphino)propane, 0.76 g of palladium acetate and 680 ml of dimethylformamide and the resulting mixture was reacted at 70 to 85° C. for two days. The reactant was treated by a normal method to obtain 40 g of 2,7-diacetylnaphthalene. 4.62 g of this 2,7-diacetylnaphthalene was reacted with 7.87 g of 8-amino-7-quinoline carboaldehyde and 7.9 g of potassium hydroxide in 220 ml of ethanol at 60° C. and a reactant was treated by a normal method to obtain 4.44 g of 2,7-di(1,10-phenanthroline-2-yl)naphthalene. 5.48 g of this 2,7-di(1,10-phenanthroline-2-yl)naphthalene was reacted with 22.6 ml of phenyl lithium (2.0 M cyclohexane-ether solution) in 200 ml of toluene at room temperature for 2 days and a reactant was treated by a normal method. The obtained product was reacted with 100 g of manganese dioxide in 400 ml of dichloromethane at room temperature for 2.5 hours and a reactant was treated by a normal method to obtain 0.93 g of E-57.

Workup

  1. additiona reactant was treated by a normal method

Sources & evidence

ORD record
ord-994dcb0646214d5b83c6a478ea8fab2e
Source dataset
uspto-grants-2012_02
Patent number
US08114529B2

Linked notes

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