Sodium Hydroxide → 3-Phenyl-3-(pyridazin-4-yl)propanoic acid

HRID 512196Notes

Reaction equation

HRID 512196 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][N:17]=[N:16][CH:15]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][N:17]=[N:16][CH:15]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86716222Ethyl 3-phenyl-3-(pyridazin-4-yl)propanoate

Product 1

HCID 867162233-Phenyl-3-(pyridazin-4-yl)propanoic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-phenyl-3-(pyridazin-4-yl)propanoate (1.0 g, 3.9 mmol) in MeOH (20 mL) was added 2N NaOH (6 mL, 11.7 mmol), the resulting mixture was stirred at room temperature overnight. MeOH was removed under reduced pressure and pH adjusted to 4-5 by aq. HCl (2N), extracted with AcOEt (6×100 ml), the combined organic layer was washed with brine, dried over Na2SO4 and concentrated to get the 3-phenyl-3-(pyridazin-4-yl)propanoic acid (750 mg, yield: 84%). 1H NMR (CDCl3 400 MHz): δ9.27 (d, J=1.2 Hz, 1H), 9.09 (dd, J=4.0, 1.2 Hz, 1H), 7.67 (dd, J=5.6, 2.4 Hz, 1H), 7.41-7.36 (m, 2H), 7.34-7.27 (m, 2H), 7.24-7.18 (m, 1H), 4.48 (t, J=8.0 Hz, 1H), 3.27-3.15 (m, 1H), 3.10-3.00 (m, 1H).

Workup

  1. customMeOH was removed under reduced pressure
  2. extractionextracted with AcOEt (6×100 ml)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ab7a3aadc2740afa584fb8818eb0920
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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