Thionyl Chloride → 2-(3-Chloromethylphenoxy)methylquinoline

HRID 2248879Notes

Reaction equation

HRID 2248879 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(Cl)Cl.CN(C)C=O>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:20]=[CH:19][CH:18]=1)[CH2:2][Cl:23]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 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 washed with sodium bicarbonate solution, dried, concentrated in vacuo and the crude product purified by silica gel HPLC to yield 12.1 g 3-(2-quinolinylmethyloxy)benzylchloride as a pale yellow solid.

Workup

  1. washThe solution is washed with sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customthe crude product purified by silica gel HPLC

Sources & evidence

ORD record
ord-be978a42c5c944889daebd4684a11d04
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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