4,7-Diphenyl-1,10-phenanthroline → HCID 18628390, compound

HRID 1367801Notes

Reaction equation

HRID 1367801 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:27]=[CH:26][N:25]=[C:24]3[C:15]=2[CH:16]=[CH:17][C:18]2[C:23]3=[N:22][CH:21]=[CH:20][C:19]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:10][CH:9]=1>CO.C(Cl)Cl>[C:1]1([C:26]2[CH:27]=[C:14]([C:11]3[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=3)[C:15]3[C:24](=[C:23]4[C:18](=[CH:17][CH:16]=3)[C:19]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:20][CH:21]=[N:22]4)[N:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 178506676HCID 178506676, compound

Product 1

HCID 18628390HCID 18628390, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This yellow compound was prepared in a process analogous to the synthesis of PBP in which 2 equivalents of phenyllithium were used for each equivalent of bathophenanthroline. The clean product was obtained after running chromatography in a silica/mixture of methanol/CH2Cl2 (1:1) column with a yield of 75 percent. 1H NMR (500 MHz, CDCl3), ppm: 9.26 (d, J=7.7 Hz, 1H), 8.37 (d, J=7.0 Hz, 2H), 8.04 (s, 1H), 7.82 (m, 2H), 7.59-7.45 (m, 14H). Analysis for mono-PBP.⅛CH2Cl2. Found: C, 86.10, H, 4.50, N, 6.79. Calculated: C, 86.33, H, 4.87, N, 6.68.

Workup

  1. customThe clean product was obtained

Sources & evidence

ORD record
ord-75dcae6762514539aebfa94cf194a4fa
Source dataset
uspto-grants-2011_02
Patent number
US07893352B2

Reaction notes

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