Thionyl Chloride → 6-(Chloromethyl)quinoline

HRID 1815177Notes

Reaction equation

HRID 1815177 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11]O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:15]>C1C=CC=CC=1>[Cl:15][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15143856-Hydroxymethylquinoline

Product 1

HCID 146661986-(Chloromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Quinolin-6-yl-methanol (7.7 g, 48 mmol) was dissolved in benzene (3 mL) and SOCl2 (20 mL) was added at 0° C. The mixture was stirred at RT for 1 h, then heated to reflux and stirred an additional 1 h. The mixture was cooled to RT and the solid was filtered to give the 6-chloromethyl-quinoline.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred an additional 1 h
  4. temperatureThe mixture was cooled to RT
  5. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-031866f33fce461c973a7e7e640d531c
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

Loading…