Hydrochloric Acid → 2-(4-((6-Fluoro-2-quinolinyl)oxy)phenoxy)-N-(4-(trifluoromethyl)phenyl)propanamide

HRID 1073020Notes

Reaction equation

HRID 1073020 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[CH:5]2.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=3)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 150701622-(4-((6-Fluoro-2-quinolinyl)oxy)phenoxy)propionyl chloride

Product 1

HCID 150701632-(4-((6-Fluoro-2-quinolinyl)oxy)phenoxy)-N-(4-(trifluoromethyl)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5 mmol of 2-(4-((6-fluoro-2-quinolinyl)oxy)phenoxy)propionyl chloride, prepared using substantially the procedure of Step A of Example 1 from the corresponding acid in 5 milliliters (ml) of methylene chloride, was slowly added to an ice-cooled solution comprising 0.89 grams (g) (5.5 mmol) of 4-aminobenzotrifluoride and 0.61 g (6 mmol) of triethylamine in 30 ml of methylene chloride. The reaction mixture was stirred at 0° C. for 30 minutes then at room temperature for 2 hours. The mixture was poured into a dilute aqueous HCl solution. The organic layer was separated, washed with water, then washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and evaporated to dryness. The residual solid was taken up in boiling methylcyclohexane, filtered and filtrate allowed to cool to give 1.68 g (71 percent of theoretical) of the above-named product as colorless crystals. The product melted at 153°-155° C. and its structure was confirmed by its infrared (IR) and its nuclear magnetic resonance (NMR) spectrum. (Compound 3)

Workup

  1. temperaturecooled solution
  2. waitat room temperature for 2 hours
  3. customThe organic layer was separated
  4. washwashed with water
  5. washwashed with a saturated aqueous NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. filtrationfiltered
  9. temperatureto cool

Sources & evidence

ORD record
ord-1036831357124ea9bf37ad919724ffbd
Source dataset
uspto-grants-1990_11
Patent number
US04968343

Reaction notes

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