تفاعل #6775

معادلة التفاعل

2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline

LiOH.H2O

→

2-carboxy-4-oxo-7-methylquinoline

المردود 98.8%

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   أخرىthe resulting reaction mixture
3. 3
   ترشيحThe reaction mixture was filtered
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىto remove methanol
6. 6
   workup.ADDITIONdiluted with water (300 mL)
7. 7
   ترشيحThe precipitate was collected by filtration
8. 8
   غسيلwashed with water
9. 9
   أخرىdried

الإجراء التجريبي

2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline (28.5 g, 99.6 mmol) was suspended in methanol (1 L) and a solution of LiOH.H2O (20.5 g, 0.5 mol) in water (200 mL) was added to the solution. The resulting reaction mixture was stirred at ambient temperature for 0.5 hours. Pd/C (5.8 g) was added to the reaction mixture and the resulting reaction mixture was shaken under 50 Psi hydrogen overnight. The reaction mixture was filtered, concentrated under reduced pressure to remove methanol, diluted with water (300 mL) and the pH was adjusted to between pH 3 and pH 4 by 2N HCl. The precipitate was collected by filtration, washed with water and dried to afford a white solid, 2-carboxy-4-oxo-7-methylquinoline (20 g, 90%); NMR (DMSO-d6) 2.40 (s, 3), 6.60 (s, 1), 7.20 (d, 1), 7.68 (s, 1), 7.96 (d, 1) ppm.

المصدر