반응 #84064

반응 방정식

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

AlCl3

→

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

수율 18.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed overnight
2. 2
   기타The mixture was quenched with saturated NH4Cl (10 mL)
3. 3
   추출the aqueous layer was extracted with CH2Cl2/MeOH (v/v=10:1, 30 mL×3)
4. 4
   세척The combined organic layer was washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to give the crude product, which
9. 9
   기타was purified by prep-HPLC (0.1% TFA as additive)

실험 절차

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]+.

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