Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(4,5-dimethyl-2-pyridinyl)-

HRID 869890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869890
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.[C:10]1(=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[O:11]1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([N:9]2[C:10](=[O:11])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:19])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6811Phthalic AnhydrideHCID 516892Sodium BicarbonateHCID 124040134,5-Dimethylpyridin-2-amine

Produkt 1

HCID 687404971H-Isoindole-1,3(2H)-dione, 2-(4,5-dimethyl-2-pyridinyl)-Ausbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4,5-dimethylpyridin-2-amine (2.1 g, 0.02 mol) in acetic acid (40 mL) was added isobenzofuran-1,3-dione (2.5 g, 0.02 mol) at the room temperature. The mixture was heated at 90° C. overnight. The resulting solution was basified by saturated solution of NaHCO3 and extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 2-(4,5-dimethylpyridin-2-yl)-isoindoline-1,3-dione (1.7 g, 40%) 1H NMR (300 MHz, DMSO) δ 8.33 (s, 1H), 7.97-7.91 (m, 4H), 7.32 (s, 1H), 2.30 (s, 3H), 2.27 (s, 3H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-64f855316c25441c9979e7b59c08ffd1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

Notizen zur Reaktion

Wird geladen…