Acetic Anhydride → 1-Acetyl-5-iodo-6-methylindazole

HRID 13068

Reaktionsgleichung

Reaktionsgleichung von HRID 13068
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1[CH:15]=[C:14]([I:16])[C:13]([CH3:17])=[CH:12][C:10]=1[NH2:11].C([O-])(=O)C.[K+].C(O[N:29]=O)CC(C)C>C1C=CC=CC=1>[C:5]([N:11]1[C:10]2[C:9](=[CH:15][C:14]([I:16])=[C:13]([CH3:17])[CH:12]=2)[CH:8]=[N:29]1)(=[O:7])[CH3:6]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Produkt 1

HCID 593397351-Acetyl-5-iodo-6-methylindazoleAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Acetic acid anhydride (6.9 mL, 72 mmol) was added to a slurry of 2,5-dimethyl-4-iodoaniline (6.0 g, 24 mmol) and potassium acetate (2.4 g, 24 mmol) in benzene (50 mL). The mixture was heated to 80° C. and isopentylnitrit (4.8 mL, 36 mmol) was added during 20 min. The mixture was stirred at 80° C. overnight, then cooled and filtered. The filtrate was evaporated and purified by column chromatography (SiO2, dichloromethane). Product containing fractions were pooled and concentrated. The subtitle compound (1.5 g, 21%) was obtained as crystals from ethyl acetate.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. custompurified by column chromatography (SiO2, dichloromethane)
  5. additionProduct containing fractions
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-15ee512a6807457dac01a4e09db860ab
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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