1-(4-Nitrophenyl)propan-2-one → 4-Aminophenylacetone

HRID 450079

Reaction equation

HRID 450079 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 2193671-(4-Nitrophenyl)propan-2-one

Product 1

HCID 117883794-AminophenylacetoneYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(4-nitro-phenyl)-propan-2-one (150 mg) was dissolved in methanol (5 ml) and then Pd/C (50 mg) was added. The resulting reaction mixture was stirred for 10 hr at room temperature under hydrogen pressure. The reaction mixture was filtered over celite and the filtrate evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (1:9) as eluent gave 1-(4-amino-phenyl)-propan-2-one (60 mg, 48%).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered over celite
  3. customthe filtrate evaporated
  4. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-a0e0548b7b274966b0f7a67c197f26de
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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