Thionyl Chloride → 2-(3-Chloromethylphenoxy)methylquinoline

HRID 1090772Notes

Reaction equation

HRID 1090772 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O>[Cl:23][CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 145017062-(3-Chloromethylphenoxy)methylquinoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

25.6g (93.5 mmoles) of 2-(3-hydroxymethylphenoxy)methylquinoline is dissolved in 30 ml of methylene chloride and 3 drops of dimethylformamide is added. 60.7 ml of a 2.0M solution of thionyl chloride in methylene chloride is then added dropwise at 0° C. The mixture is allowed to warm to room temperature and stirred for 5 hours. The solution is worked with sodium bicarbonate solution, dried, concentrated in vacuo and the crude product purified by silica gel HPLC to yield 12.1 g 2-(3chloromethylphenoxy)methylquinoline as a pale yellow solid.

Workup

  1. customdried
  2. concentrationconcentrated in vacuo
  3. customthe crude product purified by silica gel HPLC

Sources & evidence

ORD record
ord-edaec38e1dfc4ad88de44616d5f6d358
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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