Sodium Hydroxide → 2-(5-Chloro-3-pyridyloxy)butyric acid

HRID 1374889Notes

Reaction equation

HRID 1374889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:14][CH3:15])[C:10]([O:12]C)=[O:11])[CH:5]=[N:6][CH:7]=1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:14][CH3:15])[C:10]([OH:12])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21078438Methyl 2-(5-chloro-3-pyridyloxy)butyrate

Product 1

HCID 210783782-(5-Chloro-3-pyridyloxy)butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

The product from Stage 1 (27.4 g) was treated with a solution of sodium hydroxide (9.6 g) in water (50 ml) then stirred at 90° C. for 1.5 hours. The mixture was cooled to ambient temperature, diluted with water then washed with ethyl acetate. The aqueous phase was separated, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (three times). The extracts were combined, washed with brine and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the required product as a pale brown solid, 24.8 g, m.p. 98–101° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. washthen washed with ethyl acetate
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (three times)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-342a16731a504c1497e4d5830f145717
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

Loading…