HCID 18442574, compound → HCID 18442568, compound

HRID 458803Notes

Reaction equation

HRID 458803 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[N+:22]([O-])=O)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>[Pd].CO>[NH2:22][C:13]1[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=1[C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 1

HCID 18442574HCID 18442574, compound

Product 1

HCID 18442568HCID 18442568, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2-(3,4-dichloro-phenyl)-1-(4,5-dimethoxy-2-nitro-phenyl)-ethanone (9.62 g, 25.98 mmol) and palladium on charcoal (2.88 g, 30% in mass) was added dropwise methanol (500 ml) and the resulting heterogeneous mixture was hydrogenated (1 atm) at RT for 4 days. The reaction mixture was filtered over celite, and the celite cake was washed several times with anhydrous methanol. The filtrate was then evaporated to dryness and the crude brown oil was purified by flash chromatography (dichloromethane/methanol, 360/1) to give the expected aniline derivative as a brown oil (5.04 g, 57%).

Workup

  1. customat RT
  2. customfor 4 days
  3. filtrationThe reaction mixture was filtered over celite
  4. washthe celite cake was washed several times with anhydrous methanol
  5. customThe filtrate was then evaporated to dryness
  6. customthe crude brown oil was purified by flash chromatography (dichloromethane/methanol, 360/1)

Sources & evidence

ORD record
ord-a8e123996f024ff58bb21d9328387631
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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