تفاعل #84064

معادلة التفاعل

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

AlCl3

→

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

المردود 18.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed overnight
2. 2
   أخرىThe mixture was quenched with saturated NH4Cl (10 mL)
3. 3
   استخلاصthe aqueous layer was extracted with CH2Cl2/MeOH (v/v=10:1, 30 mL×3)
4. 4
   غسيلThe combined organic layer was washed with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىto give the crude product, which
9. 9
   أخرىwas purified by prep-HPLC (0.1% TFA as additive)

الإجراء التجريبي

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]+.

المصدر