Hydrazine, (phenylmethyl)-, hydrochloride (1:1) → HCID 178507199, compound

HRID 1062814Notes

Reaction equation

HRID 1062814 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:16]#[N:17])[C:11](OCC)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[CH2:19]([NH:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.C(N(CC)CC)C>[NH2:17][C:16]1[N:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:27]=[C:11]([OH:12])[C:10]=1[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1

Participants

5

Reactant 2

HCID 14084Hydrazine, (phenylmethyl)-, hydrochloride (1:1)HCID 10900525Ethyl 2-(3,4-Methylenedioxyphenyl)cyanoacetate

Product 1

HCID 178507199HCID 178507199, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred suspension of ethyl 2-(1,3-benzodioxol-5-yl)-2-cyanoacetate (76 g) and benzylhydrazine hydrochloride (99 g) in ethanol (1300 ml), triethylamine (152 ml) was slowly added at room temperature. The solution was refluxed for two days, then concentrated under reduced pressure. To the dark residue, ethyl acetate (800 ml) and water (1000 ml) were added. The white precipitate was collected by filtration washed with water and ethyl acetate, then dried under educed pressure to give the title compound as a white solid (41 g).

Workup

  1. additionwas slowly added at room temperature
  2. temperatureThe solution was refluxed for two days
  3. concentrationconcentrated under reduced pressure
  4. additionTo the dark residue, ethyl acetate (800 ml) and water (1000 ml) were added
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-67df19edd0be4696a5ab18601fbdc38c
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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