Hydrazine hydrate (1:1) → HCID 11659290, compound

HRID 1865853Notes

Reaction equation

HRID 1865853 reaction equation
[C:1]([N:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][N:10]=[C:9]1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.NN>C(O)C.[Ni]>[C:1]([N:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][N:10]=[C:9]1[C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57978097HCID 57978097, compound

Product 1

HCID 11659290HCID 11659290, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Raney Ni (19.0 g) was added to a 500 mL 3-necked round bottom flask, followed by washing with anhydrous ethanol (30 mL×3) and then ethanol (50 mL) was added. To the suspension was added a solution of compound 4 (16.6 g, 52.0 mmol, 1.0 eq) in ethanol (230 mL). Hydrazine monohydrate (10.4 g 208 mmol, 4.0 eq) was added dropwise at 50° C., followed by heating to 75° C. for 5 min. Upon cooling to room temperature, the catalyst was removed by suction filtration through celite. The filtrate was evaporated to dryness, then co-evaporated with toluene twice and finally dried at 60-65° C. for 30 min under reduced pressure to give compound 1 (14.8 g) in 99% yield.

Workup

  1. washby washing with anhydrous ethanol (30 mL×3)
  2. additionethanol (50 mL) was added
  3. temperatureUpon cooling to room temperature
  4. customthe catalyst was removed by suction filtration through celite
  5. customThe filtrate was evaporated to dryness
  6. customfinally dried at 60-65° C. for 30 min under reduced pressure

Sources & evidence

ORD record
ord-d116dd0029c14fdbaa9be38fd1f1cca1
Source dataset
uspto-grants-2009_12
Patent number
US07629347B2

Reaction notes

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