Thionyl Chloride → 4-(Chloromethyl)quinoline

HRID 599358Notes

Reaction equation

HRID 599358 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1>ClCCl>[Cl:3][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 804794-(Hydroxymethyl)quinoline

Product 1

HCID 123557014-(Chloromethyl)quinolineYield 116.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (12 mL, 170 mmol) was added dropwise for 15 minutes to a solution of 4-(hydroxymethyl)quinoline (Reference Compound No. 3-1, 13 g 82 mmol) in anhydrous dichloromethane (200 mL) under ice-cooling, and the mixture was stirred for 5 hours at room temperature. The solvent was evaporated under reduced pressure, and the resulting solid was filtered off with ethyl acetate, and washed to give 17 g of mixture containing the title Reference Compound, as a yellow-white solid.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationthe resulting solid was filtered off with ethyl acetate
  4. washwashed

Sources & evidence

ORD record
ord-f614f3fcbaa94baf972edb94ac8cefc1
Source dataset
uspto-grants-2011_03
Patent number
US07897774B2

Reaction notes

Loading…