Ethyl Acetate → [(2-Fluorophenyl)hydrazono]malonic acid

HRID 1875472Notes

Reaction equation

HRID 1875472 reaction equation
O.[C:2]([O-:9])(=[O:8])[C:3]([C:5]([O-:7])=[O:6])=O.[Na+].[Na+].Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21].C(OCC)(=O)C>Cl.O>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][N:21]=[C:3]([C:5]([OH:7])=[O:6])[C:2]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 71317420Mesoxalicacidmonohydratedisodiumsalt

Product 1

HCID 21813250[(2-Fluorophenyl)hydrazono]malonic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Sodium mesoxalate monohydrate (2.21 g, 12.3 mmol) was dissolved in 1 M hydrochloric acid (50 ml) to give a colourless cloudy solution. 2-Fluoro-phenylhydrazine hydrochloride (2.00 g, 12.3 mmol) was added portionwise at room temperature to the stirred mixture. A yellow precipitate formed, the mixture was diluted with water (50 ml) and stirring continued overnight. Ethyl acetate (150 ml) was added, the phases were mixed vigorously until the solids had dissolved. The phases were separated and the aqueous phase was washed with ethyl acetate (50 ml). The combined organic phases were dried over magnesium sulfate, filtered and the solvent removed under vacuum. The title compound was isolated as a yellow powder (2.55 g, 11.7 mmol, 92%). LCMS: m/z 227 [M−H]+.

Workup

  1. customto give a colourless cloudy solution
  2. customA yellow precipitate formed
  3. additionthe phases were mixed vigorously until the solids
  4. dissolutionhad dissolved
  5. customThe phases were separated
  6. washthe aqueous phase was washed with ethyl acetate (50 ml)
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-5d83111cba0a4d8191472c4da1a9ee66
Source dataset
uspto-grants-2012_11
Patent number
US08309552B2

Reaction notes

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