Dichloromethane → 5-(Chloromethyl)isoquinoline hydrochloride

Reaction equation

[CH:1]1[C:10]2[C:5](=[C:6]([CH2:11]O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.O=S(Cl)[Cl:15].[CH2:17](Cl)[Cl:18]>>[ClH:15].[Cl:18][CH2:17][C:9]1[CH:8]=[CH:7][CH:6]=[C:1]2[C:10]=1[CH:5]=[CH:4][CH:3]=[N:2]2.[ClH:15].[Cl:15][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 24386Thionyl Chloride

HCID 12832770Isoquinolin-5-ylmethanol2×

Product 2

HCID 681822905-(Chloromethyl)isoquinoline hydrochlorideYield 42%

HCID 681824835-(chloromethyl)quinoline hydrochloride

Procedure

To a solution of isoquinolin-5-ylmethanol MDE 32040 (0.53 g, 3.33 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (4.9 mL, 67.4 mmol) and the mixture was stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 5-(chloromethyl)quinoline hydrochloride MDE 32044 as an off-white solid (301 mg, 42% yield).