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

HRID 2380078Notes

Reaction equation

HRID 2380078 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>CO.[Pd]>[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

4

Reactant 1

HCID 10487947o-Nitrophenyl cyclopropyl ketone

Product 1

HCID 10931741(2-Aminophenyl)(cyclopropyl)methanoneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of o-nitrophenyl cyclopropyl ketone (100 mg, 0.52 mmole) and a catalytic amount of 10% Pd on carbon in methanol is stirred under hydrogen at atmospheric pressure until reaction is complete by TLC. The reaction mixture is filtered and the filtrate is concentrated in vacuo to give a bright yellow oil. The oil is flash chromatographed to give the title product as an off-white crystalline solid, 72 mg (85% yield), identified by 1HNMR.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto give a bright yellow oil
  4. customchromatographed

Sources & evidence

ORD record
ord-f4dd3b685703471b91bc5a3a86856b9a
Source dataset
uspto-grants-1994_11
Patent number
US05364968

Reaction notes

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