Hydrazine → HCID 14166615, compound

HRID 1354862Notes

Reaction equation

HRID 1354862 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[NH:18][C:19](=[O:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CCOC(C)=O.CCO.[Ni]>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([NH:18][C:19](=[O:21])[CH3:20])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 14166614N-(2-benzyloxy-4-nitro-phenyl)-acetamide

Product 1

HCID 14166615HCID 14166615, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2-Benzyloxy-4-nitro-phenyl)-acetamide (418) (5 g, 17.5 mmol) was dissolved in a mixture of EtOAc (25 mL) and EtOH (25 mL). The solution was chilled on an ice bath. Raney Nickel (5 mL, 50% slurry in water) followed immediately by anhydrous hydrazine (10 mL) were added. Violent bubbling was observed. The ice bath was removed after 10 minutes and the slurry continued to stir until all bubbling had ceased (˜30 minutes). LC-MS and TLC (Rf: 0.15 compared to Rf: 0.5 for compound 418 in 1:1 hexane/EtOAc) indicated complete reduction at this point. The reaction mixture was passed through a plug of silica gel, concentrated, dissolved in EtOAc (250 mL), washed with water (2×75 mL), brine (2×75 mL), dried over MgSO4 and concentrated to give the desired product (419) as a beige solid (3.82 g, 14.9 mmol, 85.3% yield). LC-MS (ESI): (exact mass: 256.12) m/e=257.1 [M+1]+ (100%), 513.2 [2M+1]+ (15%).

Workup

  1. temperatureThe solution was chilled on an ice bath
  2. additionwere added
  3. customViolent bubbling
  4. customThe ice bath was removed after 10 minutes
  5. custom(˜30 minutes)
  6. concentrationconcentrated
  7. dissolutiondissolved in EtOAc (250 mL)
  8. washwashed with water (2×75 mL), brine (2×75 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9af13e58336e443da5a340ca59295e6f
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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