Sodium Hydroxide → 2-[3-(Aminocarbonyl)-2,4-difluorophenoxy]acetic acid

HRID 415579Notes

Reaction equation

HRID 415579 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([F:17])=[C:6]([CH:13]=[CH:14][C:15]=1[F:16])[O:7][CH2:8][C:9]([O:11]C)=[O:10])=[O:3].[OH-].[Na+]>O.C(O)(C)C>[NH2:1][C:2]([C:4]1[C:5]([F:17])=[C:6]([CH:13]=[CH:14][C:15]=1[F:16])[O:7][CH2:8][C:9]([OH:11])=[O:10])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59402740Methyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate

Product 1

HCID 594026632-[3-(Aminocarbonyl)-2,4-difluorophenoxy]acetic acidYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Methyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate (7 mmol, 1 equiv.) was added to a solution of NaOH (1 g, 25 mmol, 3.6 equiv.) in water (20 ml) and isopropyl alcohol (5 ml). The mixture was stirred under reflux for 1.5 h, diluted with water (40 ml) and extracted with CH2Cl2 (40 ml). The aqueous phase was acidified to pH 1 with conc. HCl solution. The precipitant solid was filtered and dried in vacuo to give the desired compound (130 mg, 8%), mp 152-153° C. HPLC-MS (method 1): m/z 312 [M−H+2CH3CN]−, Rt=0.91 min.

Workup

  1. temperatureunder reflux for 1.5 h
  2. extractionextracted with CH2Cl2 (40 ml)
  3. filtrationThe precipitant solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-22c02ce96289449dbd2954ace8f22d61
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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