Dichloromethane → HCID 86761894, compound

HRID 444607Notes

Reaction equation

HRID 444607 reaction equation
[C:1]1([CH:41]2[C:54]3[CH2:53][CH2:52][C:51]4[C:46](=[N:47][C:48]([C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)=[CH:49][C:50]=4[C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:45]=3[NH:44][C:43]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[C:42]2[C:73]#[N:74])[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[C:20]3[CH2:19][CH2:18][C:17]4[C:12](=[N:13][C:14]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:15][C:16]=4[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:11]=3[NH:10][C:9]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:8]2[C:39]#[N:40])[CH:2]=1.C(Cl)Cl>C(O)COCCO.[Pd]>[C:3]1([C:7]2[C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:13]4)[N:10]=[C:9]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:8]=2[C:39]#[N:40])[CH:4]=[CH:5][CH:6]=[C:1]([C:41]2[C:54]3[C:45](=[C:46]4[C:51](=[CH:52][CH:53]=3)[C:50]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[CH:49][C:48]([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[N:47]4)[N:44]=[C:43]([C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)[C:42]=2[C:73]#[N:74])[CH:2]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 86761895HCID 86761895, compound

Product 1

HCID 86761894HCID 86761894, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8117Diethylene GlycolSolvent

Procedure

suspension of 4,4′-(1,3-phenylene)bis(2,7,9-triphenyl-1,4,5,6-tetrahydro-1,10-phenanthroline-3-carbonitrile) (5) in 2 L diethyleneglycol was heated until total dissolution. 10 g Pd/C was then slowly added, and the reaction was refluxed for 72 hours with argon bubbling directly in the solution. The reaction was monitored by TLC (Silica Gel; CH2Cl2). The starting material's spot (rf: 0.8, blue-green under 366 nm) converted into a blue fluorescent spot (rf: 0.9). Once the starting material spot has disappeared, the reaction was stopped, and the suspension cooled to room temperature.

Workup

  1. temperaturewas heated until total dissolution
  2. temperaturethe reaction was refluxed for 72 hours with argon bubbling directly in the solution

Sources & evidence

ORD record
ord-b54fcff3c6354d968538bcb17b8771e8
Source dataset
uspto-grants-2013_07
Patent number
US08475686B2

Reaction notes

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