Potassium Hydroxide → 1,10-Phenanthroline

HRID 2251142Notes

Reaction equation

HRID 2251142 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.[OH-].[K+].O1CCO[CH2:18][CH2:17]1>>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]3[C:2]=2[N:1]=[CH:18][CH:17]=[CH:12]3)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 110520988-Aminoquinoline-7-carboxaldehyde

Product 1

HCID 13181,10-Phenanthroline

Procedure

4.0 g of propellane, 3.3 g of aluminium chloride and 2.0 ml of acetyl chloride were added to 200 ml of 1,2-dichloroethane, and reaction carried out for 1.5 hours at room temperature and then for 6 hours at 60° C. By treatment in the normal way, 3.26 g of the triacetyl-propellane was obtained. 1.41 g of this triacetyl derivative was reacted with 1.50 g of 8-amino-7-quinolinecarbaldehyde and 1.5 g of potassium hydroxide in dioxane at 60° C. and, by treatment in the normal way, Phen-5 (1.32 g) shown below was obtained.

Workup

  1. custombelow was obtained

Sources & evidence

ORD record
ord-37e63e4f03634a108331c3a39a2c4f4a
Source dataset
uspto-grants-2008_01
Patent number
US07318966B2

Reaction notes

Loading…