o-Nitrophenyl cyclopropyl ketone → (2-Aminophenyl)(cyclopropyl)methanone

HRID 2380082Notes

Reaction equation

HRID 2380082 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-])=O)=[O:5])[CH2:3][CH2:2]1.[H][H]>[Pd].C1(C)C=CC=CC=1>[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:12])=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 10487947o-Nitrophenyl cyclopropyl ketoneHCID 178418361HCID 178418361, compound

Product 1

HCID 10931741(2-Aminophenyl)(cyclopropyl)methanoneYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of the 23.6% toluene solution of o-nitrophenyl cyclopropyl ketone obtained in Example 7 (232.3 g, 0.286 mole ketone) and 2.86 g of 5% Pd/C catalyst is placed under H2 at 32-56 psig in a Parr hydrogenator. The hydrogen uptake is monitored and when the reaction is complete, the reaction mixture is filtered and concentrated in vacuo to give the title product, 39.5 g, 86.3% pure by HPLC analysis (73.9% yield).

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-950113a94915408481544756d6647aa3
Source dataset
uspto-grants-1994_11
Patent number
US05364968

Reaction notes

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