Thionyl Chloride → 3-(Chloromethyl)-7-methoxyquinoline hydrochloride

HRID 1620181Notes

Reaction equation

HRID 1620181 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([CH2:13]O)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.COC1C=C2C(C=C(C=O)C=N2)=CC=1.O=S(Cl)[Cl:31]>C(Cl)Cl>[ClH:31].[Cl:31][CH2:13][C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 112524387-Methoxyquinoline-3-carbaldehydeHCID 68182191(7-Methoxyquinolin-3-yl)methanol

Product 1

HCID 681822023-(Chloromethyl)-7-methoxyquinoline hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-methoxyquinolin-3-yl)methanol MDE 32006 (219 mg, 1.16 mmol) in dry CH2Cl2 (12 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.68 mL, 23.16 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)-7-methoxyquinoline hydrochloride MDE 32012 as an off-white solid (246 mg, 87% 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-089ebce6a71b435fb48c4366efbcd77b
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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