Sodium Hydroxide → Ethyl 2-(4-amino-2,5-difluorophenyl)acetate

HRID 1879111Notes

Reaction equation

HRID 1879111 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([CH:11](C(OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]([F:22])[CH:5]=1>O.C(O)C>[NH2:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]([F:22])[CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59163383Diethyl (4-amino-2,5-difluorophenyl)propanedioate

Product 1

HCID 23512379Ethyl 2-(4-amino-2,5-difluorophenyl)acetateYield 40.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydroxide (903 mg, 22.58 mmol) in water (7 ml) was added to a solution of diethyl (4-amino-2,5-difluorophenyl)propanedioate (4.32 g, 15.05 mmol) in ethanol (35 ml). The reaction mixture was heated to 90° C. under argon for 1 hr. The reaction mixture was allowed to cool and then the solvent was evaporated. The residue was acidified (2M HCl, 200 ml) and then extracted with ethyl acetate (200 ml). The organic layer was dried (Mg SO4) and the solvent evaporated. The residue was purified by flash chromatography (Biotage SP4, 40+M, 0→25% ethyl acetate/hexane) to afford the title compound as a pale yellow oil (1.3 g). MS (ES+) m/z 216 [M+H+] (C10H11FNO2).

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated
  3. extractionextracted with ethyl acetate (200 ml)
  4. dry with materialThe organic layer was dried (Mg SO4)
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography (Biotage SP4, 40+M, 0→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-256b113159114a07970978559d0ae97a
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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