HCID 67159330, compound → HCID 59291167, compound

HRID 2234365Notes

Reaction equation

HRID 2234365 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[O:6][CH:7]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH:7]2[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8]2)[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

4

Reactant 1

HCID 67159330HCID 67159330, compound2×

Product 1

HCID 59291167HCID 59291167, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(3-methoxy-4-nitro-phenoxy)-1-methyl-pyrrolidine (Intermediate 46; 5.50 g, 20.68 mmol) in ethanol (125 mL) under nitrogen was added in one portion the Pd/C catalyst (10%, 500 mg). The resulting mixture was evacuated and backfilled with nitrogen (×4) before hydrogen gas was introduced via a balloon. The reaction mixture was stirred at room temperature for 18 hrs. The catalyst was removed by filtration through celite and the filtrate concentrated under reduced pressure to give a the title compound as a light red oil (4.74 g, 100%)

Workup

  1. customThe resulting mixture was evacuated
  2. additionwas introduced via a balloon
  3. customThe catalyst was removed by filtration through celite
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-30aaea0ed8f744d097b3e718ed346d82
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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