Reaktion #305640

Reaktionsgleichung

N,O-dimethylhydroxyamine-HCl

3-Carboxyindazole

carbonyldiimidazole

→

N-methoxy-N-methyl-1H-indazole-3-carboxamide

Ausbeute 81.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to rt
2. 2
   Temperaturthe mixture was heated to 65° C. overnight
3. 3
   TemperaturThe reaction was cooled
4. 4
   Sonstigequenched with water
5. 5
   Extraktionextracted with CH2Cl2
6. 6
   Waschenwashed with water
7. 7
   SonstigeThe combined organic phase was dried
8. 8
   Einengenconcentrated

Vorschrift

3-Carboxyindazole (10 g, 61.7 mmol) in DMF (100 mL) was treated with carbonyldiimidazole (11 g, 67.84 mmol) at rt with gas evolution for 15 min, after which the reaction mixture was heated up to 65° C. for 2 hours. After cooling to rt, N,O-dimethylhydroxyamine-HCl (4.14 g, 67.8 mmol) was added and the mixture was heated to 65° C. overnight. The reaction was cooled, quenched with water, extracted with CH2Cl2 and washed with water. The combined organic phase was dried and concentrated to afford N-methoxy-N-methyl-1H-indazole-3-carboxamide (10.3 g, 81.4%).

Quelle