Water → 1-(1H-Indazol-3-yl)ethan-1-one

HRID 414925

Reaktionsgleichung

Reaktionsgleichung von HRID 414925
CON(C)[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5].[CH3:16][Mg]Br.O.[Cl-].[NH4+]>O1CCCC1>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:4](=[O:5])[CH3:16])=[N:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 156841691-(1H-Indazol-3-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round-bottomed flask, 2.4 g of N-methoxy-N-methyl-1H-indazole-3-carboxamide are placed in 140 ml of tetrahydrofuran at 0° C. and under argon. 19 ml of methylmagnesium bromide (3M in ethyl ether) are added dropwise. The mixture is stirred for one hour at 0° C. and 20 h at ambient temperature. It is cooled to 0° C. and 80 ml of water and 40 ml of a saturated solution of ammonium chloride are added. The mixture is extracted with 40 ml of ethyl acetate. The organic phase is washed with 40 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 1.6 g of compound are obtained.

Aufarbeitung

  1. temperatureIt is cooled to 0° C.
  2. extractionThe mixture is extracted with 40 ml of ethyl acetate
  3. washThe organic phase is washed with 40 ml of a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution

Quellen und Nachweise

ORD-Eintrag
ord-be03b3ea900a4de18284983fe9b1078b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088765B2

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