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ChemicalBook CAS DataBase List 4-Chloroquinoline 1-oxide

4-Chloroquinoline 1-oxide synthesis

6synthesis methods

Product Name:4-Chloroquinoline 1-oxide
CAS Number:4637-59-6
Molecular formula:C9H6ClNO
Molecular Weight:179.6

611-35-8 Synthesis

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Yield:4637-59-6 99%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 0 - 20;

Steps:

6 Intermediate 11 (I11): 4-Chloroquinoline 1-oxide

To a solution of 4-chloroquinoline (2.05 g, 12.53 mmol) in DCM (30 mL) at 0 ^οC was added m-CPBA (3.24 g, 18.80 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with 1M NaOH until pH = 10. The aqueous layer was extracted with DCM three times and the combined organic extracts were dried over Na₂SO₄, filtered and concentrated under pressure. The crude product was used without further purification. White solid (2.24 g, 99%). ¹H NMR (400 MHz, DMSO-d₆) δ 8.62 - 8.56 (m, 2H), 8.24 - 8.19 (m, 1H), 7.97 - 7.86 (m, 2H), 7.70 (d, J = 6.6 Hz, 1H).

References:

WO2021/105497,2021,A1 Location in patent:Page/Page column 115; 117; 138-139