Reaktion #725831

Reaktionsgleichung

sodium hydroxide

2-Amino-2,3-dimethylbutyronitrile

2,3-quinolinedicarboxylic anhydride

4-picoline

sodium hydroxide

sulfuric acid

sodium hydroxide

hydrogen peroxide

→

2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining the temperature at 40° to 43° C
2. 2
   workup.STIRRINGthe mixture stirred at 55° to 60° C. for approximately 15 minutes
3. 3
   SonstigeThe lower aqueous basic phase is separated off
4. 4
   Extraktionthe product extracted from organic phase with water
5. 5
   WaschenThe aqueous phase is washed with toluene
6. 6
   workup.STIRRINGto stir for one hour at 65° to 70° C
7. 7
   TemperaturThe mixture is cooled to 25° to 30° C.

Vorschrift

2-Amino-2,3-dimethylbutyronitrile (0.393 mol) is added over 40 minutes to a stirred solution of 2,3-quinolinedicarboxylic anhydride (0.376 mol) in 4-picoline (338 g, 3.63 mol) and toluene (52 g), while maintaining the temperature at 40° to 43° C. The reaction mixture is stirred at 40° to 43° C. for one hour. Aqueous sodium hydroxide (218 g, 25%, 1.36 mol) and then toluene 378 g) are added and the mixture stirred at 55° to 60° C. for approximately 15 minutes. The lower aqueous basic phase is separated off and the product extracted from organic phase with water. The aqueous phase is washed with toluene. A portion of the aqueous phase (25.8 g) is treated with 25% aqueous sodium hydroxide (10 g) and 3.7 equivalents of hydrogen peroxide at 65°-70° C. for one hour, then additional 50% aqueous sodium hydroxide (14.5 g) is added and the reaction mixture is allowed to stir for one hour at 65° to 70° C. The mixture is cooled to 25° to 30° C., and the pH of the mixture adjusted to 1.5 with concentrated sulfuric acid. The product 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid (17.3 g) is isolated by filtration.

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