o-Chloranil → ethyl 4-cyano-1,3-dimethyl-1H-indazole-5-carboxylate

HRID 439725

Reaktionsgleichung

Reaktionsgleichung von HRID 439725
[C:1]([C:3]1[C:4]2[C:5]([CH3:18])=[N:6][N:7]([CH3:17])[C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:2].C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>C1C=CC=CC=1>[C:1]([C:3]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH3:18])=[N:6][N:7]2[CH3:17])#[N:2]

Komponenten

4

Edukt 2

HCID 73252o-ChloranilHCID 22402928ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate

Produkt 1

HCID 22402968ethyl 4-cyano-1,3-dimethyl-1H-indazole-5-carboxylateAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate (13.5 g, 55.0 mmol), o-chloranil (16.3 g, 66.0 mmol) and dry benzene is stirred for 1.5 hours at reflux temperature, cooled and filtered. The filtrate is concentrated in vacuo, filtered through two pads of neutral alumina and evaporated to dryness to afford a yellow solid. Recrystallization from ethyl acetate affords the title product (6.33 g, 47.2%), mp 170°-175.5° C.

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. filtrationfiltered through two pads of neutral alumina
  6. customevaporated to dryness
  7. customto afford a yellow solid
  8. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7e6ef78a7e6149acbb5ce549f8594c87
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516751

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