HCID 21835835, compound → HCID 21835823, compound

HRID 1741442Notes

Reaction equation

HRID 1741442 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[CH3:29])[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]=[N+]=[N-])=[C:13]([O:23][CH3:24])[CH:12]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[CH3:29])[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][NH2:20])=[C:13]([O:23][CH3:24])[CH:12]=1

Participants

4

Reactant 1

HCID 21835835HCID 21835835, compound

Product 1

HCID 21835823HCID 21835823, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.00 g (2.5 mmol) of N-{2-(3,4-dimethylphenoxy)ethyl}-4-(2-azidoethoxy)-3-methoxyphenylacetamide obtained in step 3 was dissolved in 100 ml of methanol and thereto was added 0.40 g of 10% Pd/C. The mixture was stirred under a hydrogen atmosphere at an ambient temperature for 5 hours. The reaction mixture was passed through a Celite™ layer to remove Pd/C, and the filtrate was concentrated under a reduced pressure to produce a residue, which was recrystallized form dichloromethane/hexane to obtain 0.60 g (yield 64%) of the title compound as a white solid.

Workup

  1. customto remove Pd/C
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customto produce a residue, which
  4. customwas recrystallized form dichloromethane/hexane

Sources & evidence

ORD record
ord-103e8114aab94f8f83f2e933062ddb8b
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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