Hydrazine hydrate (1:1) → HCID 22046631, compound

HRID 1830961Notes

Reaction equation

HRID 1830961 reaction equation
O.NN.[CH3:4][O:5][C:6]1[C:7]([N+:21]([O-])=O)=[C:8]([CH:18]=[CH:19][CH:20]=1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17])=[O:10].[H][H]>[Ni].CO>[NH2:21][C:7]1[C:6]([O:5][CH3:4])=[CH:20][CH:19]=[CH:18][C:8]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17])=[O:10]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 14299928HCID 14299928, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22046631HCID 22046631, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (4.37 g, 136.4 mmol) was added dropwise to a solution of 92 (6.37 g, 22.7 mmol) in gently refluxing methanol (100 mL) over Raney nickel (2.4 g, slurry). The resulting vigorous evolution of hydrogen gas subsided after approximately 10 minutes and the reaction was deemed to be complete by TLC after 2 h. The reaction mixture was filtered through celite and the solvent evaporated. Distilled water (100 mL) was added to the residue, and the aqueous mixture was extracted with EtOAc (3×100 mL) and washed with H2O (3×100 mL) and brine (3×100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent afforded a brown glass (5.49 g, 21.8 mmol) as a single spot by TLC.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent evaporated
  3. additionDistilled water (100 mL) was added to the residue
  4. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  5. washwashed with H2O (3×100 mL) and brine (3×100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f95129952293490e9477f88873ba46e5
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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