Glycerol → 7-(Trifluoromethyl)quinoline

HRID 1808329

Reaction equation

HRID 1808329 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].O[CH2:18][CH:19]([CH2:21]O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.II>[F:6][C:7]([F:15])([F:16])[C:8]1[CH:9]=[C:10]2[C:12]([CH:18]=[CH:19][CH:21]=[N:11]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 73753-(Trifluoromethyl)anilineHCID 10340Sodium Carbonate

Product 1

HCID 4596147-(Trifluoromethyl)quinolineYield 22.13%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

Conc. sulfuric acid (4.56 g; 1.5 equiv.) was added dropwise to a mixture of 3-(trifluoromethyl)aniline (5 g; 1 equiv.), glycerol (5.14 g; 1.8 equiv.) and iodine (150 mg). The resulting reaction mixture was stirred for 1 hour at 80-90° C. and for 3 hours at 160-170° C. When the conversion was complete, the reaction mixture was diluted at room temperature with 100 ml of water, neutralised with sodium carbonate and extracted 4× with 200 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, 10% EtOAc/hexane). 7-(Trifluoromethyl)quinoline (1.35 g; 22.13%) was obtained in the form of a white crystalline solid.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted 4× with 200 ml of dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-1d27ae53d74e492db446c5b28b6471dd
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Linked notes

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