Thionyl Chloride → 3-Chloromethyl-6-methoxyquinoline hydrochloride

HRID 1620294Notes

Reaction equation

HRID 1620294 reaction equation
[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]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 304667(6-Methoxyquinolin-3-yl)methanol2×

Product 1

HCID 190420403-Chloromethyl-6-methoxyquinoline hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. concentrationThe residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-74a051c81787438492246b64add3db34
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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