Hydrazine hydrate (1:1) → Ethyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate

HRID 58884

Reaktionsgleichung

Reaktionsgleichung von HRID 58884
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.O.[NH2:14]N.C[N:17]([CH:19](OC)OC)C>C(O)C>[NH:14]1[C:2]2[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]=2[CH:19]=[N:17]1

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Produkt 1

HCID 58243478Ethyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-oxocyclohexanecarboxylate (50 g, 0.29 mol) in DMF-DMA (275 mL) was heated at 110° C. for 12 h. The mixture was concentrated and hydrazine hydrate (73.5 g, 1.47 mol) in ethanol (1000 mL) was heated under reflux overnight. Most of ethanol was removed and the remaining mixture was treated with water (400 mL). The resulting mixture was extracted with EtOAc (400 ml×2). The combined organic layers were washed with brine (400 mL) and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1) to afford crude ethyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate (18 g) as a colorless solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. temperatureunder reflux overnight
  3. customMost of ethanol was removed
  4. additionthe remaining mixture was treated with water (400 mL)
  5. extractionThe resulting mixture was extracted with EtOAc (400 ml×2)
  6. washThe combined organic layers were washed with brine (400 mL)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-209f6e2d4b424b73ba61e5ea63342ae0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434761B2

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