Pyrrole → HCID 136336905, compound

HRID 1904196Notes

Reaction equation

HRID 1904196 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1>C(O)(=O)CC>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]2[C:17]3[NH:13][C:14]([C:9]([C:8]4[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=4)=[C:14]4[N:13]=[C:17]([C:9]([C:8]5[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=5)=[C:14]5[NH:13][C:17](=[C:9]([C:8]6[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:12][CH:11]=6)[C:14]6[CH:15]=[CH:16][C:17]=2[N:13]=6)[CH:16]=[CH:15]5)[CH:16]=[CH:15]4)=[CH:15][CH:16]=3)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 136336905HCID 136336905, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

para-Acetamidobenzaldehyde (10.0g) is added to refluxing propionic acid (100ml): an orange solution gradually forms. Pyrrole (4.1g) is added continuously, and the dark solution is refluxed for 1 hour, and kept at 0° C. overnight. A dark tarry material is removed by filtration and the filtrate is evaporated to dryness. The residue is dissolved in chloroform and chromatographed on silica gel G eluted with 10% methanol in chloroform. The red fluorescing fractions are combined and the porphyrin HK9 is obtained as a purple solid (0.021g) on evaporation.

Workup

  1. temperaturethe dark solution is refluxed for 1 hour
  2. customA dark tarry material is removed by filtration
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe residue is dissolved in chloroform
  5. customchromatographed on silica gel G
  6. washeluted with 10% methanol in chloroform

Sources & evidence

ORD record
ord-e022acfc6098445cb20c8b9ec3f991e5
Source dataset
uspto-grants-1989_06
Patent number
US04837221

Reaction notes

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