Thionyl Chloride → 4-(Chloromethyl)-2-methylquinoline

HRID 61434

Reaction equation

HRID 61434 reaction equation
O[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[CH:4]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10149033(2-Methylquinolin-4-yl)methanol

Product 1

HCID 115357194-(Chloromethyl)-2-methylquinolineYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-hydroxymethyl-2-methyl quinoline (7.0 g, 40 mmol) was dissolved in chloroform (150 mL) and cooled to 0° C., thionyl chloride (15.0 mL) was added slowly at this temperature and then the reaction mixture was allowed to warm up to room temperature and stirred overnight. The solvent was removed in-vacuo and the residue was titureted with ethyl acetate/ethyl ether to provide 9.0 g (100%) of 4-chloromethyl-2-methyl quinoline as an HCl salt. MS (ESI): 191.9 (M+H+).

Workup

  1. temperatureto warm up to room temperature
  2. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-668a3648814747428598077790518b17
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Linked notes

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