Sodium Hydroxide → Ethyl 2-(4-amino-3-fluorophenyl)acetate

HRID 889486Notes

Reaction equation

HRID 889486 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[F:19].[OH-].[Na+]>C(O)C.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[F:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58399565Diethyl (4-amino-3-fluorophenyl)propanedioate

Product 1

HCID 59760056Ethyl 2-(4-amino-3-fluorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Diethyl (4-amino-3-fluorophenyl)propanedioate (11.85 g, 44.1 mmol) was dissolved in ethanol (80 ml) and treated with NaOH (2.6 g, 1.5 eq) dissolved in 18 ml of water to give a pink solution. This was heated to 90° C. for 1 hour until complete. Heating continued for 1 further hour, and then cooled to room temperature. Solvent evaporated and acidified with 2N HCl. Extracted with ethyl acetate (3×100 ml). Organics washed with brine and dried over MgSO4. Evaporated to give the title compound as a yellow oil which crystallised slowly on standing (6.6 g).

Workup

  1. customto give a pink solution
  2. temperatureHeating
  3. temperaturecooled to room temperature
  4. customSolvent evaporated
  5. extractionExtracted with ethyl acetate (3×100 ml)
  6. washOrganics washed with brine
  7. dry with materialdried over MgSO4
  8. customEvaporated

Sources & evidence

ORD record
ord-4ce4dac263bb431db9d0bf41181923ea
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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