1-Naphthaldehyde → HCID 16158959, compound

HRID 1060505Notes

Reaction equation

HRID 1060505 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6]1([CH:16]=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>CS(C)=O>[C:6]1([C:16]2[C:2]3[NH:1][C:5](=[CH:4][CH:3]=3)[C:16]([C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:7]=3)=[C:5]3[N:1]=[C:2]([CH:3]=[CH:4]3)[C:16]([C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:7]=3)=[C:2]3[NH:1][C:5]([CH:4]=[CH:3]3)=[C:16]([C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:7]=3)[C:5]3=[N:1][C:2]=2[CH:3]=[CH:4]3)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 8027Pyrrole2×

Product 1

HCID 16158959HCID 16158959, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Tetra-(1-naphthyl) porphine (designated TNP) was prepared from the following reactants in a DMSO solvent: pyrrole and 1-naphthaldehyde. Prior to mixing the reactants, pyrrole was distilled under an argon atmosphere with the fraction boiling at 130° C. collected. The 1-naphthaldehyde was distilled under vacuum to purify. A mixture of 6.0 g of pyrrole, 13.7 g of 1-naphthaldehyde, and 120 ml or DMSO were heated at reflux for 2 hours. The reaction solution was cooled and the DMSO solvent partially removed under vacuum. The solid that was present was filtered off and washed with 60 ml of methanol, 60 ml of hot water, and 12 ml of cold methanol. The resulting solid was then dried in a vacuum oven at ambient temperature overnight.

Workup

  1. distillationwas distilled under an argon atmosphere with the fraction boiling at 130° C.
  2. customcollected
  3. distillationThe 1-naphthaldehyde was distilled under vacuum
  4. customto purify
  5. additionA mixture of 6.0 g of pyrrole, 13.7 g of 1-naphthaldehyde, and 120 ml or DMSO
  6. temperaturewere heated
  7. temperatureat reflux for 2 hours
  8. temperatureThe reaction solution was cooled
  9. customthe DMSO solvent partially removed under vacuum
  10. filtrationThe solid that was present was filtered off
  11. washwashed with 60 ml of methanol, 60 ml of hot water, and 12 ml of cold methanol
  12. customThe resulting solid was then dried in a vacuum oven at ambient temperature overnight

Sources & evidence

ORD record
ord-eb88862f74e7436983a998fdd2a20df5
Source dataset
uspto-grants-2003_02
Patent number
US06524379B2

Reaction notes

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