Pyrrole → HCID 136204851, compound

HRID 1161962Notes

Reaction equation

HRID 1161962 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.[NH:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1>C(O)(=O)CC>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:13]3[NH:9][C:10]([C:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[C:10]4[N:9]=[C:13]([C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[C:10]5[NH:9][C:13](=[C:7]([C:5]6[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=6)[C:10]6[CH:11]=[CH:12][C:13]=2[N:9]=6)[CH:12]=[CH:11]5)[CH:12]=[CH:11]4)=[CH:11][CH:12]=3)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 8027PyrroleHCID 5731171-Methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 136204851HCID 136204851, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

To a refluxing solution of propionic acid (200 mL) and 1-methylpyrazole-4-carboxaldehyde (48, 0.92 g, 8.32 mmol), prepared according to literature procedure (Finar, I. L.; Lord, G. H. J. Chem. Soc. 1957, 3314-3315), was added pyrrole (0.63 mL, 8.32 mmol). The reaction was covered with foil and was heated under reflux for 3.5 h. Upon cooling the reaction mixture was exposed to air overnight. The propionic acid was then removed by vacuum distillation. The crude residue was dissolved in 5% MeOH/CH2Cl2, then adsorbed onto silica gel (5.3 g). Purification by column chromatography (5% MeOH/CH2Cl2) provided porphyrin 49 as a purple solid (231 mg, 17.5%): 1H NMR (300 MHz, DMSO-d6) δ −2.74 (s, 2 H), 4.28 (s, 12 H), 8.31 (s, 4 H), 8.67 (s, 4 H), 9.16 (s, 8 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 h
  3. temperatureUpon cooling the reaction mixture
  4. customThe propionic acid was then removed by vacuum distillation
  5. dissolutionThe crude residue was dissolved in 5% MeOH/CH2Cl2
  6. customPurification by column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a38b1ac1c23f48949475bd6f165b3522
Source dataset
uspto-grants-2010_10
Patent number
US07820644B2

Reaction notes

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