HCID 129713539, compound → HCID 131718220, compound

HRID 1656140Notes

Reaction equation

HRID 1656140 reaction equation
[N+:1]([N:4]1[C:8]2=[C:9]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:10]3[CH:11]=[CH:12][C:13]([N:48]=3)=[C:14]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:15]3[N:19]([N+:20]([O-])=O)[C:18]([C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:24]4[N:35]=[C:27]([C:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[C:5]1[CH:6]=[CH:7]2)[CH:26]=[CH:25]4)=[CH:17][CH:16]=3)([O-])=O>C1(C)C=CC=CC=1.[Ru]>[NH2:20][N:19]1[C:15]2=[C:14]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:13]3[CH:12]=[CH:11][C:10]([N:48]=3)=[C:9]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:8]3[N:4]([NH2:1])[C:5]([C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:27]4[N:35]=[C:24]([C:23]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)=[C:18]1[CH:17]=[CH:16]2)[CH:25]=[CH:26]4)=[CH:6][CH:7]=3

Participants

4

Reactant 1

HCID 129713539HCID 129713539, compound

Product 1

HCID 131718220HCID 131718220, compound

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 1140TolueneSolvent

Procedure

Dinitrotetraphenylporphyrin (2.0 g 2.83 m mol) was added to a hydrogenation flask (500-ml) and dissolved in dry toluene (200-ml). To this solution was added the catalyst about 10% ruthenium on alumina pellets (4.0 g, from Engelhard Industries, Iselin, N.J.). After evacuation, and flushing with hydrogen, the reduction was performed at 70° at 60 psi for 8-hr. Next, the flask was cooled to ambient temperature, filtered in the dark to remove the catalyst. The solid catalyst was washed repeatedly with toluene to obtain the product. The organic solvent was removed under reduced pressure in the dark at 50° C. to produce the crude solid residue. This residue showed one spot above the two spots near the base line for the product. An additional brown spot very close to the starting material was also observed. The residue was 1.6 g.

Workup

  1. customAfter evacuation, and flushing with hydrogen
  2. waitthe reduction was performed at 70° at 60 psi for 8-hr
  3. filtrationfiltered in the dark
  4. customto remove the catalyst
  5. washThe solid catalyst was washed repeatedly with toluene
  6. customto obtain the product
  7. customThe organic solvent was removed under reduced pressure in the dark at 50° C.
  8. customto produce the crude solid residue
  9. customAn additional brown spot very close to the starting material

Sources & evidence

ORD record
ord-1ed88f60027648ac9ca9fa9fa9a43d6e
Source dataset
uspto-grants-1993_10
Patent number
US05252698

Reaction notes

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