Thionyl Chloride → 3-(Chloromethyl)quinoline hydrochloride

HRID 1620173Notes

Reaction equation

HRID 1620173 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11]O)[CH:2]=1.O=S(Cl)[Cl:15]>C(Cl)Cl>[ClH:15].[Cl:15][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12662983(Quinolin-3-yl)methanol2×

Product 1

HCID 145481263-(Chloromethyl)quinoline hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of quinolin-3-ylmethanol MDE 32002 (0.26 g, 1.63 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (2.4 mL, 33.1 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 3-(chloromethyl)quinoline hydrochloride MDE 32004 as an off-white solid (301 mg, 85% 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-2938207264d9453894decae14f2d491b
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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