Diethyl (ethoxymethylene)malonate → 288251-62-7

HRID 2095807Notes

Reaction equation

HRID 2095807 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[K+].[K+].C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:19])[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 22228038288251-62-7Yield 48.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (4-fluorophenyl)hydrazine•hydrochloride (3 g, 18 mmol) and water (75 mL) were added potassium carbonate (5.6 g, 40 mmol) and diethyl ethoxymethylenemalonate (4.8 g, 22 mmol), and the mixture was heated under reflux for 7 hr. After cooling to room temperature, the mixture was washed with ethyl acetate. 6N Aqueous hydrochloric acid solution was added to the separated aqueous layer under ice-cooling. The precipitated solid was collected by filtration, washed with water and ethyl acetate/hexane (1/10), and dried under reduced pressure to give the title compound (2.2 g, 48%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. washthe mixture was washed with ethyl acetate
  4. addition6N Aqueous hydrochloric acid solution was added to the separated aqueous layer under ice-
  5. temperaturecooling
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water and ethyl acetate/hexane (1/10)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-49e35ae4005d40fca09197084167709c
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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