Dichloromethane → 6-(Chloromethyl)isoquinoline hydrochloride

HRID 1620164Notes

Reaction equation

HRID 1620164 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11]O)=[CH:3][CH:2]=1.O=S(Cl)[Cl:15].[CH2:17](Cl)[Cl:18]>>[ClH:15].[Cl:18][CH2:17][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2.[ClH:15].[Cl:15][CH2:9][C:8]1[CH:11]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH:10]=[N:1][CH:2]=[CH:3]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 804794-(Hydroxymethyl)quinoline

Product 2

HCID 200819696-(Chloromethyl)quinoline hydrochlorideHCID 681822816-(Chloromethyl)isoquinoline hydrochlorideYield 93%

Procedure

To a solution of quinolin-4-ylmethanol MDE 32046 (0.24 g, 1.51 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 (2.3 mL, 31.2 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 6-(chloromethyl)quinoline hydrochloride MDE 32048 as an off-white solid (301 mg, 93% yield).

Workup

  1. customThe volatiles were then removed at 40° C. under vacuum
  2. concentrationthe residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-da02cedbe64f49a994cf13afefdb86c5
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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