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Dimethyl 5-aminoisophthalate → 1,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate

HRID 2071137
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2071137
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[CH:14]=[C:15]([CH:20]=1)[C:16]([O:18][CH3:19])=[O:17]>C(O)(=O)C>[N:10]1([C:11]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[C:13]([CH:12]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:3]=[CH:7][CH:6]=[CH:5]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 66831Dimethyl 5-aminoisophthalateHCID 790982,5-Dimethoxytetrahydrofuran

Produkt 1

HCID 189451711,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylateAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

2,5-dimethoxytetrahydrofuran (0.74 ml, 0.76 g, 5.74 mmol, 1.2 eq) was added to a stirred suspension of dimethyl 5-aminoisophthalate (1.0 g, 4.78 mmol, 1 eq) in 7 ml acetic acid under Ar. The mixture was heated to reflux at 135° C. After 45 min the reaction was cooled to RT, and the solvent was removed in vacuo. The residue was stirred in saturated aqueous NaHCO3/EtOAc overnight. The layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (×1), water (×2), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.288 g (1.11 mmol, 23% yield) of the product. A significant amount of crude product was also collected.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureAfter 45 min the reaction was cooled to RT
  3. customthe solvent was removed in vacuo
  4. customThe layers were separated
  5. washThe organic layer was washed with saturated aqueous NaHCO3 (×1), water (×2), brine (×1)
  6. dry with materialdried over Na2SO4
  7. filtrationThe inorganics were filtered off
  8. customthe solvent was removed in vacuo
  9. customPurification via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0734fe30bbcc410a814a58f2832283d6
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299267B2

Notizen zur Reaktion

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