Hydrazine hydrate (1:1) → HCID 90408190, compound

HRID 871085Notes

Reaction equation

HRID 871085 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:16]=1)[NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=1.O.NN>CO.O.[Ni]>[Br:1][C:2]1[CH:16]=[C:6]([NH:7][CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=2)[C:5]([NH2:17])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90409847HCID 90409847, compound

Product 1

HCID 90408190HCID 90408190, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 12A (1.777 g, 5.45 mmol) in methanol (30 mL) was added hydrazine hydrate (0.74 g, 15.26 mmol), followed by 50% Raney® nickel in water (200 mg) and the mixture was heated at 50° C. for 60 minutes. After cooling, diatomaceous earth was added and the slurry was filtered through diatomaceous earth with dichloromethane. Concentration provided the crude title compound which was used without further purification. MS (ESI) m/z 295.9 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. additiondiatomaceous earth was added
  3. filtrationthe slurry was filtered through diatomaceous earth with dichloromethane
  4. concentrationConcentration

Sources & evidence

ORD record
ord-afc3d3f4c0114a47916f910b70d4d5cd
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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