Thionyl Chloride → 4-Hydroxy-7-trifluoromethyl-3-(chloromethyl)-quinoline

HRID 574132Notes

Reaction equation

HRID 574132 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:16]O.S(Cl)([Cl:20])=O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:16][Cl:20]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178519811HCID 178519811, compound

Product 1

HCID 1785161894-Hydroxy-7-trifluoromethyl-3-(chloromethyl)-quinolineYield 82.6%

Procedure

4-Hydroxy-7-trifluoromethyl-3-(hydroxymethyl)-quinoline (3.6 grams) was added to an excess (5.9 grams) of thionyl chloride and the mixture was refluxed for 1 hour. Excess thionyl chloride was then evaporated and the remaining residue was crystallized from hexane to give 4-hydroxy-7-trifluoromethyl-3-(chloromethyl)-quinoline (3.2 grams).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customExcess thionyl chloride was then evaporated
  3. customthe remaining residue was crystallized from hexane

Sources & evidence

ORD record
ord-1dafdcb658d64a08a922bec02ea76dfc
Source dataset
uspto-grants-2015_05
Patent number
US09034872B2

Reaction notes

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