Methanesulfonic Acid → 1,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dione

HRID 507064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507064
ON=[CH:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)=[O:5].CS(O)(=O)=[O:18]>>[NH:6]1[C:7]2[C:15](=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH2:11]3)[C:3](=[O:18])[C:4]1=[O:5]

Komponenten

3

Edukt 2

HCID 6395Methanesulfonic AcidHCID 727406282-Hydroxyimino-N-indan-4-yl-acetamide

Produkt 1

HCID 148855691,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dioneAusbeute 72 %

Versuchsvorschrift

Add 2-Hydroxyimino-N-indan-4-yl-acetamide (5.54 g, 27.1 mmol) in small portions at 80° C. to methanesulfonic acid (21 mL). Stir the mixture at this temperature for 25 min. Cool to room temperature, pour into ice water and filter the precipitate. Dissolve the solid in warmed 1N NaOH, and neutralize with acetic acid. Filter the resulting solid and acidify the filtrate with concentrated HCl. Filter the precipitate and wash with water. Dry the solid to yield the title compound (3.80 g, 72%). MS (ES−): 186 (M−H).

Aufarbeitung

  1. filtrationfilter the precipitate
  2. dissolutionDissolve the solid in warmed 1N NaOH
  3. filtrationFilter the resulting solid
  4. filtrationFilter the precipitate
  5. washwash with water
  6. customDry the solid

Quellen und Nachweise

ORD-Eintrag
ord-e12bdf1b929c4767921567509fa5bf0d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786108B2

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