p-Toluenesulfonic acid → HCID 135512470, Verbindung

HRID 990990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990990
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C1(C)C=CC(S([NH:28][NH2:29])(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH:28]1[C:2]2[C:10]3[C:5]([CH2:4][C:3]=2[C:11]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:29]1)=[CH:6][CH:7]=[CH:8][CH:9]=3

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 15303P-ToluenesulfonylhydrazideHCID 53775483HCID 53775483, Verbindung

Produkt 1

HCID 135512470HCID 135512470, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-oxoindan-2-ylidenemethyl)phenol (1.67 g, Chem. Ber. 1901, 34, 413), p-toluenesulphonyl hydrazine (1.95 g), p-toluenesulphonic acid (0.27 g) and ethanol (15 ml) was boiled under reflux for 72 hours. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica using petroleum ether, b.p. 60-80° C./ethyl acetate (1:1) as the mobile phase. Appropriate fractions were collected, combined and evaporated to give a residue which was triturated with petroleum ether, b.p. 60-80° C., to give a solid which was crystallized from ethanol to give 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol, m.p. 266-268° C.

Aufarbeitung

  1. temperatureunder reflux for 72 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica
  4. customAppropriate fractions were collected
  5. customevaporated
  6. customto give a residue which
  7. customwas triturated with petroleum ether, b.p. 60-80° C.
  8. customto give a solid which
  9. customwas crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6f5fb2ed6ffb420f828104a108e24f6b
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462036B1

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