Thionyl Chloride → 3-Chloromethyl-6-methoxyquinoline hydrochloride
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13]O)=[CH:6]2.O=S(Cl)[Cl:17]>C(Cl)Cl>[ClH:17].[Cl:17][CH2:13][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of (6-methoxyquinolin-3-yl)methanol SLA 47088A (0.476 g, 2.5 mmol) in dry CH2Cl2 (25 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (3.65 mL, 50.4 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-6-methoxyquinoline hydrochloride SLA 47088B as a yellow solid (0.60 g, 98% yield).