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

HRID 1463217

Reaktionsgleichung

Reaktionsgleichung von HRID 1463217
[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-a532c404b2d14e46975e091be15fca4a
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300479

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