Potassium Hydroxide → 1,10-Phenanthroline
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]=1Participants
Procedure
2.5 g of 6,6′-bis(trifluoromethanesulphonyloxy)-3,3,3′,3′-tetramethyl-1,1′-spirobiindane, 2.2 g of 4-acetylphenylboronic acid, 12 ml of 2M sodium carbonate and 0.40 g of tetrakis(triphenylphosphine)palladium(0) were added to a solvent mixture of 50 ml of toluene and 30 ml of ethanol, and then refluxing carried out for 12 hours under nitrogen so that a Suzuki coupling reaction was conducted and, by treatment in the normal way, 1.5 g of 6,6′-bis(4-acetylphenyl)-3,3,3′,3′-tetramethyl-1,1′-spirobiindane was obtained. 1.50 g of this diacetyl derivative was reacted with 1.26 g of 8-amino-7-quinolinecarbaldehyde and 0.9 g of potassium hydroxide in dioxane at 60° C. and, by treatment in the normal way, Phen-4 (1.40 g) shown below was obtained. 1H-NMR (CDCl3, ppm): 9.21 (d, 2H), 8.35 (d, 4H), 8.25 (t, 4H), 8.09 (d, 2H), 7.80−7.59 (m, 12H), 7.34 (d, 2H), 7.24 (d, 2H), 2.46 (d, 4H), 1.52 (s, 6H), 1.46 (s, 6H)
Workup
- custombelow was obtained
Sources & evidence
- ORD record
- ord-4ccdefe4ec104ec8a5cb8f4aa0eff6e0
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07318966B2
Reaction notes
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