Hydrochloric Acid → HCID 83401207, compound

HRID 1748431Notes

Reaction equation

HRID 1748431 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:4]=1[NH:11][NH2:12].C(O[CH:16]=[C:17]([C:23]([CH3:25])=O)[C:18]([O:20]CC)=[O:19])C.[OH-].[Na+]>C(O)C>[F:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:4]=1[N:11]1[C:23]([CH3:25])=[C:17]([C:18]([OH:20])=[O:19])[CH:16]=[N:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 2777968HCID 2777968, compound

Product 1

HCID 83401207HCID 83401207, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed solvent of 1N hydrochloric acid aqueous solution (120 ml) and ethanol (120 ml), were added 2,3,4-trifluorophenylhydrazine (9.3 g) and ethyl 2-(ethoxymethylene)acetoacetate (10.7 g) prepared according to a method described in J. Chem. Soc. Perkin trans. I, 1875 (1988), and the mixture was stirred at reflux temperature for three hours. Next, sodium hydroxide (2.8 g) was added and the mixture was further stirred for an hour. Ethanol was evaporated in vacuo, the organic layer was separated with toluene, hydrochloric acid was added to the aqueous layer and the precipitated solid was collected by filtration to give the titled compound (10 g).

Workup

  1. customprepared
  2. temperatureat reflux temperature for three hours
  3. stirringthe mixture was further stirred for an hour
  4. customEthanol was evaporated in vacuo
  5. customthe organic layer was separated with toluene, hydrochloric acid
  6. additionwas added to the aqueous layer
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-27208da68b284fb2bc09e18d30241d51
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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