2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 11139333, compound

HRID 1463979Notes

Reaction equation

HRID 1463979 reaction equation
C(O[CH:4]=[C:5]([C:11]#[N:12])[C:6]([O:8]CC)=[O:7])C.[CH2:13]([O:15][CH:16]([O:20][CH2:21][CH3:22])[CH2:17][NH:18][NH2:19])[CH3:14]>C(O)C.O>[CH2:13]([O:15][CH:16]([O:20][CH2:21][CH3:22])[CH2:17][N:18]1[C:11]([NH2:12])=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=[N:19]1)[CH3:14]

Participants

5

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 322952(2,2-Diethoxyethyl)hydrazine

Product 1

HCID 11139333HCID 11139333, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of ethyl ethoxymethylenecyanoacetate (21.7 g) in ethanol (65 ml) was added dropwise a solution of hydrazinoacetaldehyde diethyl acetal (19 g) in water (19 ml) under ice-cooling. The mixture was stirred at 80° C. for 1.5 hours and evaporated to remove ethanol. To the residue was 4N sodium hydroxide (64 ml), and the mixture was refluxed for 1 hour. The mixture was adjusted to pH 3.5 with concentrated hydrochloric acid at 10°-20° C., and the resulting precipitate was collected by filtration to give 1-(2,2-diethoxyethyl)-4-carboxy-5-aminopyrazole (8.60 g).

Workup

  1. temperaturecooling
  2. customevaporated
  3. customto remove ethanol
  4. temperaturethe mixture was refluxed for 1 hour
  5. customwas adjusted to pH 3.5 with concentrated hydrochloric acid at 10°-20° C.
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-489c8a7f5b4e494b9d87d268c258d8d9
Source dataset
uspto-grants-1994_04
Patent number
US05302712

Reaction notes

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