反応 #6775

反応方程式

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

LiOH.H2O

→

2-carboxy-4-oxo-7-methylquinoline

収率 98.8%

溶媒

methanol

water

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   その他the resulting reaction mixture
3. 3
   ろ過The reaction mixture was filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他to remove methanol
6. 6
   workup.ADDITIONdiluted with water (300 mL)
7. 7
   ろ過The precipitate was collected by filtration
8. 8
   洗浄washed with water
9. 9
   その他dried

実験手順

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.

出典