HCID 18407216, compound → N-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

HRID 1016576Notes

Reaction equation

HRID 1016576 reaction equation
[N:1]([CH2:4][C:5]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6])=[N+]=[N-]>CO.[Pt]=O>[NH2:1][CH2:4][C:5]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]

Participants

4

Reactant 1

HCID 18407216HCID 18407216, compound

Product 1

HCID 53640241N-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyanilineYield 39.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

To a solution of 647 mg of N-azidoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline in 7 ml of methanol was added 20 mg of platinum oxide, followed by stirring under a hydrogen atmosphere at room temperature overnight. The reaction mixture was filtered through Celite, and after concentration under reduced pressure, purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:6) and recrystallized from ethyl acetate-isopropyl ether to give 0.24 g of N-aminoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationafter concentration under reduced pressure
  3. custompurified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:6)
  4. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-b663fdfcedab4ca5aa41b07f59358ef9
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

Loading…