Pyrrole → HCID 136395930, compound

HRID 1488440Notes

Reaction equation

HRID 1488440 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=O)[CH:6]=1.[NH:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1>C(O)(=O)CC>[CH3:1][O:2][C:3]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[C:18]3[NH:14][C:15]([C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:13])[CH:6]=4)=[C:15]4[N:14]=[C:18]([C:11]([C:7]5[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:13])[CH:6]=5)=[C:15]5[NH:14][C:18](=[C:11]([C:7]6[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:13])[CH:6]=6)[C:15]6[CH:16]=[CH:17][C:18]=2[N:14]=6)[CH:17]=[CH:16]5)[CH:17]=[CH:16]4)=[CH:16][CH:17]=3)[CH:8]=[CH:9][CH:10]=1)=[O:13]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 11819590Methyl 2-(3-formylphenyl)acetate

Product 1

HCID 136395930HCID 136395930, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
60 °C

Procedure

17.82 g (0.10 mol) of (3-formylphenyl)-acetic acid methyl ester (B RN 3231441) is dissolved in 300 ml of propionic acid and the solution is heated to 60° C. 6.71 g (0.10 mol) of pyrrole is instilled slowly and the dark solution is stirred for 1 hour at 110° C. After cooling, it is completely concentrated by evaporation in a vacuum, the residue is taken up in dichloromethane and shaken out with saturated aqueous sodium bicarbonate solution. After the drying of the organic phase on sodium sulfate, it is filtered and concentrated by evaporation, and the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol. The residue of the product fractions that are concentrated by evaporation is recrystallized from isopropanol.

Workup

  1. temperatureAfter cooling
  2. concentrationit is completely concentrated by evaporation in a vacuum
  3. stirringshaken out with saturated aqueous sodium bicarbonate solution
  4. customAfter the drying of the organic phase on sodium sulfate, it
  5. filtrationis filtered
  6. concentrationconcentrated by evaporation
  7. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol
  8. concentrationThe residue of the product fractions that are concentrated by evaporation
  9. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-528817921a714e108df2a1fb86d48030
Source dataset
uspto-grants-1997_10
Patent number
US05674467

Reaction notes

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