Acetic Anhydride → Methyl 6-chloro-1H-indazole-4-carboxylate

HRID 1909327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909327
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C.[N:26](OC(C)(C)C)=O.C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)Cl>[Cl:12][C:10]1[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]2[CH:13]=[N:26][NH:1][C:2]=2[CH:11]=1

Komponenten

7

Edukt 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 68295455Methyl 3-amino-5-chloro-2-methylbenzoate

Produkt 1

HCID 24728139Methyl 6-chloro-1H-indazole-4-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (1 equiv.) in chloroform (13 mL per 1 mmol), potassium acetate (1.05 equiv.) and acetic anhydride (2 equiv.) were added and reaction mixture stirred at room temperature for 12 h. After this time, tert-butyl nitrite (4 equiv.) and 18-crown-6 (0.35 equiv.) were added and the reaction stirred again at 65° C. for 3 h. On completion, the reaction mixture was cooled to room temperature, diluted with chloroform (500 mL) and washed with sat. sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford the title compound (yield 90-95%).

Aufarbeitung

  1. customreaction mixture
  2. stirringthe reaction stirred again at 65° C. for 3 h
  3. temperatureOn completion, the reaction mixture was cooled to room temperature
  4. washwashed with sat. sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a22e0e0d4edf4a04952b6ea3c3a3e30f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598167B1

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