Sodium Hydroxide → 2-[2-Fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionic acid

HRID 542091Notes

Reaction equation

HRID 542091 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([O:16][C:17]2[CH:26]=[N:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[N:18]=2)[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8]CC)=[O:7].[OH-].[Na+]>C(O)(C)C.O1CCCC1.O>[F:1][C:2]1[CH:15]=[C:14]([O:16][C:17]2[CH:26]=[N:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[N:18]=2)[CH:13]=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 13578011Ethyl 2-[2-fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate

Product 1

HCID 135780132-[2-Fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionic acidYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl 2-[2-fluoro-4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate (3.23 g; 8.27 mmole) was dissolved in a warm mixture of isopropanol (150 ml) and tetrahydrofuran (30 ml). The solution was allowed to cool to a temperature of 25° C. and a solution of sodium hydroxide (0.34 g) in water (10 ml) was added slowly with stirring. The reaction mixture was stirred at room temperature for a period of 10 minutes and then aqueous 2M sodium hydroxide (0.5 ml) was added and the solution was stirred at room temperature for 5 hours. The solvent was removed from the reaction mixture by evaporation under reduced pressure and the residue was dissolved in water. The aqueous solution was treated with aqueous 2M hydrochloric acid until acidic and the precipitated product was collected by filtration and air dried. The product was recrystallised from toluene to give the title compound (1.83 g; 61%), mp 132°-138° C. The assigned structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for a period of 10 minutes
  2. stirringthe solution was stirred at room temperature for 5 hours
  3. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. additionThe aqueous solution was treated with aqueous 2M hydrochloric acid until acidic and the precipitated product
  6. filtrationwas collected by filtration and air
  7. customdried
  8. customThe product was recrystallised from toluene

Sources & evidence

ORD record
ord-baa9a10d7ad340b8b005f6586f802c7b
Source dataset
uspto-grants-1987_04
Patent number
US04655819

Reaction notes

Loading…