Acetic Anhydride → 1H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl ester

HRID 1854103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854103
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14]([O-:17])(=O)[CH3:15].[K+].C(OC(=O)C)(=O)C.[N:26](OC(C)(C)C)=O.C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)Cl>[C:14]([N:1]1[C:2]2[CH:11]=[C:10]([Br:12])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=2[CH:13]=[N:26]1)(=[O:17])[CH3:15]

Komponenten

7

Edukt 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Produkt 1

HCID 682954331H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl esterAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61.5 mmol) in chloroform (150 mL), was added potassium acetate (6.32 g, 64.4 mmol) and acetic anhydride (12.6 g, 122.9 mmol) and reaction mixture was stirred at room temperature for 12 h. After this time, tert-butyl nitrite (25.3 g, 246.1 mmol) and 18-crown-6 (5.7 g, 21.5 mmol) were added and reaction stirred again at 65° C. for 3 h. On completion, the reaction mass 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 (18 g, 98.3%).

Aufarbeitung

  1. customreaction
  2. stirringstirred again at 65° C. for 3 h
  3. temperatureOn completion, the reaction mass 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-4f002414fc664016a372f82af4da6be1
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962620B2

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