Sulfuric Acid → Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-

HRID 2353925

Reaktionsgleichung

Reaktionsgleichung von HRID 2353925
ON=[CH:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)=[O:5].S(=O)(=O)(O)[OH:17]>>[NH:6]1[C:7]2[C:15](=[CH:14][C:13]3[CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[C:3](=[O:17])[C:4]1=[O:5]

Komponenten

3

Edukt 2

HCID 1118Sulfuric AcidHCID 722820052-Hydroxyimino-N-indan-5-yl-acetamide

Produkt 1

HCID 22560824Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-Ausbeute 77 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Add 2-Hydroxyimino-N-indan-5-yl-acetamide (4.66 g, 22.84 mmol) in small portions at 65° C. to concentrated sulfuric acid (22 mL) and heat the mixture at 80° C. for 15 minutes. Cool to room temperature, pour into ice water (200 mL) and filter the precipitate. Dissolve the solid in warmed ethanol and leave to cool overnight. Filter the precipitate and wash with ethyl ether. Dry the solid to yield the title compound (3.3 g, 77%). 1H NMR (DMSO-d6, 300 MHz) δ 1.98 (quintuplet, J=7.7 Hz, 2H), 2.76 (t, J=7.7 Hz, 2H), 2.85 (t, J=7.7 Hz, 2H), 6.74 (s, 1H), 7.28 (s, 1H). MS (ES−): 186 (M−H).

Aufarbeitung

  1. temperatureCool to room temperature
  2. filtrationfilter the precipitate
  3. dissolutionDissolve the solid in warmed ethanol
  4. customleave
  5. temperatureto cool overnight
  6. filtrationFilter the precipitate
  7. washwash with ethyl ether
  8. customDry the solid

Quellen und Nachweise

ORD-Eintrag
ord-13b2e193704f4b339faf59bcec1d924b
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749992B2

Verknüpfte Notizen

Wird geladen…