Réaction #84064

Équation de réaction

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

AlCl3

→

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

Rendement 18.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was refluxed overnight
2. 2
   AutreThe mixture was quenched with saturated NH4Cl (10 mL)
3. 3
   Extractionthe aqueous layer was extracted with CH2Cl2/MeOH (v/v=10:1, 30 mL×3)
4. 4
   LavageThe combined organic layer was washed with brine
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   Autreto give the crude product, which
9. 9
   Autrewas purified by prep-HPLC (0.1% TFA as additive)

Mode opératoire

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]+.

Source