Acetic Anhydride → HCID 58437297, Verbindung

HRID 881593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881593
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:20]=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23]O.C(OC(=O)C)(=O)C.[OH-].[Na+]>O1CCCC1.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 58437409HCID 58437409, Verbindung

Produkt 1

HCID 58437297HCID 58437297, VerbindungAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-formyl-1H-indole-5-carboxylic acid benzyl ester (4.3 g) and pyridine (4.8 g) in tetrahydrofuran (60 ml) was added hydroxylamine hydrochloride (1.6 g) at room temperature and this mixture was stirred at 80° C. overnight. Acetic anhydride was added to reaction mixture at the same temperature and this mixture was stirred for 8 hours. After cooling to ambient temperature, 1 mol/L sodium hydroxide solution (20 mL) was added to this mixture and resulting mixture was extracted with diethyl ether. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.8 g).

Aufarbeitung

  1. stirringthis mixture was stirred for 8 hours
  2. temperatureAfter cooling to ambient temperature
  3. customresulting mixture
  4. extractionwas extracted with diethyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4dc95cd17c0547da82a180164fb1d772
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993616B2

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