反应 #84064

反应方程式

3-chloro-4-(6-methoxyquinolin-2-yl)benzoic acid

AlCl3

→

3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid

收率 18.0%

溶剂

CH2Cl2

反应条件

后处理

1. 1
   温度The reaction mixture was refluxed overnight
2. 2
   其他The mixture was quenched with saturated NH4Cl (10 mL)
3. 3
   萃取the aqueous layer was extracted with CH2Cl2/MeOH (v/v=10:1, 30 mL×3)
4. 4
   洗涤The combined organic layer was washed with brine
5. 5
   干燥dried over Na2SO4
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他to give the crude product, which
9. 9
   其他was purified by prep-HPLC (0.1% TFA as additive)

实验过程

To a suspension of 3-chloro-4-(6-methoxyquinolin-2-yl)benzoic acid (150 mg, 0.479 mmol) in anhydrous CH2Cl2 (5 mL) was added AlCl3 (320 mg, 2.40 mmol). The reaction mixture was refluxed overnight. The mixture was quenched with saturated NH4Cl (10 mL) and the aqueous layer was extracted with CH2Cl2/MeOH (v/v=10:1, 30 mL×3). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to give the crude product, which was purified by prep-HPLC (0.1% TFA as additive) to give 3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid (25 mg, yield 18%). 1H NMR (DMSO, 400 MHz): δ 10.20 (brs, 1H), 8.30 (d, J=8.4 Hz, 1H), 8.10-8.00 (m, 2H), 7.95 (d, J=9.2 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.38 (dd, J=6.4, 2.8 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), MS (ESI): m/z 299.9 [M+H]+.

来源