Thionyl Chloride → HCID 68182227, compound

HRID 1620175Notes

Reaction equation

HRID 1620175 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([CH2:13]O)[CH:7]=[N:8]2.O=S(Cl)[Cl:17]>C(Cl)Cl>[ClH:17].[Cl:17][CH2:13][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182185HCID 68182185, compound

Product 1

HCID 68182227HCID 68182227, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-methoxyquinolin-3-yl)methanol CCH 34144-3 (80 mg, 423 μmol) 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 (0.60 mL, 8.27 mmol) and the mixture was stirred for 2 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)-5-methoxyquinoline hydrochloride CCH 341448 as an off-white solid (87 mg, 84% 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-19acb9766ac243b1b74a43163463a6fa
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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