(2,5-Dichlorophenyl)hydrazine → 1-Allyl-2-[(2,5-dichloro-phenyl)-hydrazono]-cyclopentanecarboxylic acid ethyl ester

HRID 1297262Notes

Reaction equation

HRID 1297262 reaction equation
[C:1]([C:6]1([CH2:12][CH:13]=[CH2:14])[CH2:10][CH2:9][CH2:8][C:7]1=O)([O:3][CH2:4][CH3:5])=[O:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[NH:23][NH2:24].C([O-])(=O)C.[Na+]>CO>[CH2:4]([O:3][C:1]([C:6]1([CH2:12][CH:13]=[CH2:14])[CH2:10][CH2:9][CH2:8][C:7]1=[N:24][NH:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[Cl:15])=[O:2])[CH3:5]

Participants

5

Reactant 3

HCID 9366(2,5-Dichlorophenyl)hydrazineHCID 517045Sodium AcetateHCID 109104522-Carbethoxy-2-allylcyclopentanone

Product 1

HCID 866039761-Allyl-2-[(2,5-dichloro-phenyl)-hydrazono]-cyclopentanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-carbethoxy-2-allylcyclopentanone (110 mg, 0.55 mmol) in 1 mL of methanol was added (2,5-dichloro-phenyl)-hydrazine (89 mg, 0.50 mmol) and sodium acetate (62 mg, 0.75 mmol). The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated and adding 10 mL of ethyl acetate diluted the residue. The organic solution was washed with 5 mL of water and 5 mL of brine. The organic layer was dried over sodium sulfate and concentrated to give the crude product, which was directly used in next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadding 10 mL of ethyl acetate
  3. additiondiluted the residue
  4. washThe organic solution was washed with 5 mL of water and 5 mL of brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a3e6bf253ea441fda6f8a7a732f98461
Source dataset
uspto-grants-2007_07
Patent number
US07250441B2

Reaction notes

Loading…