Hydrazine hydrate (1:1) → HCID 69142509, compound

HRID 1455838Notes

Reaction equation

HRID 1455838 reaction equation
O.NN.[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:22])[C:11]2[C:16]([C:17]=1[Cl:18])=[CH:15][C:14]([N+:19]([O-])=O)=[CH:13][CH:12]=2)=[O:8])[CH3:5]>CO.C1(C)C=CC=CC=1.[Ni]>[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:22])[C:11]2[C:16]([C:17]=1[Cl:18])=[CH:15][C:14]([NH2:19])=[CH:13][CH:12]=2)=[O:8])[CH3:5]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69142291HCID 69142291, compound

Product 1

HCID 69142509HCID 69142509, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a refluxing mixture of hydrazine hydrate (10.8 ml, 222 mmol) and Raney Ni (6 g) in MeOH (200 mL) was slowly added the product of step (b) (12.6 g), and the refluxing was continued for 6 hours. After cooling to room temperature, the Raney Ni was removed by filtration through Celite, and the solvent was removed in vacuo to give the crude product. The residue was dissolved in toluene (100 mL), and concentrated in vacuo. The residue was again dissolved in toluene (100 mL), and concentrated in vacuo, the residue was suspended in diethyl ether, and the product was collected by filtration to afford 11.3 g of the title compound.

Workup

  1. customthe Raney Ni was removed by filtration through Celite
  2. customthe solvent was removed in vacuo
  3. customto give the crude product
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was again dissolved in toluene (100 mL)
  6. concentrationconcentrated in vacuo
  7. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-a83aa81804b74476b30189ede248ed0c
Source dataset
uspto-grants-2009_01
Patent number
US07482368B2

Reaction notes

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