Ethyl 2-cyano-3-ethoxy-2-butenoate → HCID 22227925, compound

HRID 1744467Notes

Reaction equation

HRID 1744467 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[C:10]([C:12](=[C:18](OCC)[CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]>C(O)C>[NH2:11][C:10]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[C:18]([CH3:19])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 69982(4-Fluorophenyl)hydrazine

Product 1

HCID 22227925HCID 22227925, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluorophenylhydrazine (25 g) and ethyl 2-cyano-3-ethoxy-3-methylacrylate (32 g) were stirred in ethanol (130 ml) at a refluxing temperature for 3 h. The solvent was evaporated and diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (10.7 g), melting point: 129–131° C.

Workup

  1. customThe solvent was evaporated
  2. additiondiisopropyl ether was added to the residue
  3. customcrystallization
  4. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-c80da76929914a6ea140a74e5d07cd97
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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