4,7-Diphenyl-1,10-phenanthroline → HCID 11375703, compound

HRID 1367804Notes

Reaction equation

HRID 1367804 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:20]=[CH:19][N:18]=[C:17]3[C:8]=2[CH:9]=[CH:10][C:11]2[C:16]3=[N:15][CH:14]=[CH:13][C:12]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:3][CH:2]=1>CO.C(Cl)Cl>[C:21]1([C:12]2[C:11]3[C:16](=[C:17]4[C:8](=[CH:9][CH:10]=3)[C:7]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)=[CH:20][C:19]([C:16]3[CH:17]=[CH:8][CH:9]=[CH:10][C:11]=3[CH3:12])=[N:18]4)[N:15]=[C:14]([C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=3[CH3:7])[CH:13]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 728124,7-Diphenyl-1,10-phenanthroline

Product 1

HCID 11375703HCID 11375703, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This yellow compound was prepared in a process analogous to the synthesis of m-TBP. However, the reaction product consisted of mono-substituted and di-substituted bathophenanthroline. O-TBP was obtained after running chromatography in a silica/mixture of methanol/CH2Cl2 (1:1) column as the first eluent in a 20 percent yield. Mono-o-TBP was obtained as the second eluent in a 50 percent yield. 1H NMR (500 MHz, CDCl3), ppm: 7.97 (s, 2H), 7.85 (s, 2H), 7.77 (s, 2H), 7.64-7.59 (m, 4H), 7.95-7.50 (m, 6H), 7.35 (m, 6H), 2.65 (s, 6H). Analysis for o-TBP.⅛CH2Cl2. Found: C, 87.03, H, 5.41, N, 5.23. Calculated: C, 87.51, H, 5.44, N, 5.35.

Workup

  1. customThis yellow compound was prepared in a process analogous to the synthesis of m-TBP
  2. customO-TBP was obtained
  3. customMono-o-TBP was obtained as the second eluent in a 50 percent yield

Sources & evidence

ORD record
ord-247c309aaf2a4dfb9210ffa30ffce82a
Source dataset
uspto-grants-2011_02
Patent number
US07893352B2

Reaction notes

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