HCID 45121157, compound → Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 4-amino-

HRID 536471Notes

Reaction equation

HRID 536471 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:11][C:10](=[O:12])[C:8]=2[CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:11][C:10](=[O:12])[C:8]=2[CH:9]=1

Participants

4

Reactant 1

HCID 45121157HCID 45121157, compound

Product 1

HCID 12067468Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 4-amino-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-nitrocyclobutabenzen-1(2H)-one (900 mg, 5.52 mmol) in ethanol (25 mL) under a stream of nitrogen was added palladium on carbon (587 mg, 10%, 0.55 mmol). The mixture was placed under a hydrogen atmosphere (balloon) and stirred at ambient temperature for 16 hours. The reaction vessel was charged with nitrogen and the mixture filtered (ethanol wash). The filtrate was concentrated and purified by chromatography (silica gel, 20% EtOAc/hexanes) to provide the title compound. MS (DCI/NH3) m/z 151 (M+NH4)+.

Workup

  1. additionThe reaction vessel was charged with nitrogen
  2. filtrationthe mixture filtered
  3. wash(ethanol wash)
  4. concentrationThe filtrate was concentrated
  5. custompurified by chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a3338652ec454ee7bd5450a6cbd9ab33
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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