Hydrochloric Acid → Propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-

HRID 359648Notes

Reaction equation

HRID 359648 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)[C:3]=1[F:21].[OH-].[Na+].[ClH:24]>O1CCOCC1>[Cl:24][C:7]1[CH:2]=[C:3]([F:21])[C:4]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20063624HCID 20063624, compound

Product 1

HCID 86315Propanoic acid, 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 13.0 g (0.04 mol) of (R) (+)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)]-methyl ester in 65 ml of dioxane are added 42 ml of 1N sodium hydroxide and the mixture is stirred for 21/2 hours at a temperature of 35°. Then it is poured onto an ice/water mixture and acidified with 22 ml of 2N hydrochloric acid. The organic material is extracted therefrom twice with ethyl acetate. The organic layers are washed with a saturated salt solution and dried over magnesium sulfate, filtered and concentrated. The residue is cristallized from ethyl acetate/hexane and yields 10.2 g (81.8% of the theory) of the above (2R) (+)-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid as white cristals, which melt at 95°-96° ([α]D20 =+37.5°±0.5°2% in acetone).

Workup

  1. extractionThe organic material is extracted
  2. washThe organic layers are washed with a saturated salt solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-866da97b45454024a6c5f125e6396da9
Source dataset
uspto-grants-1991_03
Patent number
US05002604

Reaction notes

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