1,2-Dichloroethane → HCID 17975810, compound

HRID 2108882Notes

Reaction equation

HRID 2108882 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Cl:16][CH2:17][CH2:18]Cl.C([O-])([O-])=O.[K+].[K+].[OH-].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>[Cl:16][CH2:17][CH2:18][O:13][C:7]1[C:6]2[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178516425HCID 178516425, compound

Product 1

HCID 17975810HCID 17975810, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

7-Trifluoromethyl-4-quinolinol (500 mg, 2.3 mmol) and 1,2-dichloroethane (11.6 g, 11.7 mmol) were charged in a 50 ml round-bottomed flask equipped with a magnetic stirrer. TBABr (370 mg, 1.2 mmol), K2CO3 (950 mg, 6.9 mmol), KOH (760 mg, 11.5 mmol) and water (6 mL) were added and the reaction mixture was stirred for 5 h at 70-80° C. The reaction mixture was poured in 50 mL of H2O and extracted with CH2Cl2 (150 mL). The organic layer was washed with water (30 mL), brine (2×10 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=5:5) to give after evaporation 4-(2-chloroethoxy)-7-(trifluoromethyl)quinoline 31 (150 mg, 25% yield) as a beige solid.

Workup

  1. customequipped with a magnetic stirrer
  2. extractionextracted with CH2Cl2 (150 mL)
  3. washThe organic layer was washed with water (30 mL), brine (2×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated at 30° C. to dryness
  7. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=5:5)
  8. customto give

Sources & evidence

ORD record
ord-bff92b62df6b472ea93c2e882f92a650
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

Loading…