Sodium Hydroxide → HCID 59760042, compound

HRID 889495Notes

Reaction equation

HRID 889495 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9](C(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[F:20].[OH-].[Na+]>C(O)C.O>[NH2:1][C:2]1[C:3]([F:20])=[CH:4][C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59163377HCID 59163377, compound

Product 1

HCID 59760042HCID 59760042, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Diethyl (4-amino-3,5-difluorophenyl)propanedioate (0.770 g, 2.68 mmol) was dissolved in ethanol (50 ml) and treated with sodium hydroxide (0.107 g, 2.68 mmol) in water (1.5 ml). This was heated to 90° C. for 55 minutes. Further sodium hydroxide (0.016 g, 0.40 mmol) was added to the reaction and heating continued for 15 minutes. The mixture was cooled to room temperature and evaporated. This was acidified with 2N HCl (20 ml) and extracted ×2 with ethyl acetate (25 ml). The combined organics were washed with brine (50 ml), dried over magnesium sulphate, filtered and evaporated to give the title compound as a pale brown oil (0.610 mg, 2.84 mmol, >100%). LC/MS: Rt=2.52, [MH]+ 216.

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled to room temperature
  3. customevaporated
  4. extractionextracted ×2 with ethyl acetate (25 ml)
  5. washThe combined organics were washed with brine (50 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4f17daba02f24c1d94dc0fd79b08082a
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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