2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole → 4-[(5-Propyl-1,3,4-oxadiazol-2-yl)methyl]aniline

HRID 30673Notes

Reaction equation

HRID 30673 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][C:9]2[O:10][C:11]([CH2:14][CH2:15][CH3:16])=[N:12][N:13]=2)=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].O1CCCC1>[CH2:14]([C:11]1[O:10][C:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:18][CH:17]=2)=[N:13][N:12]=1)[CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 692088952-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

Product 1

HCID 692070154-[(5-Propyl-1,3,4-oxadiazol-2-yl)methyl]anilineYield 55.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole (7.70 g), 5% palladium carbon (7.0 g) and tetrahydrofuran (200 mL) were subjected to catalytic reduction under a hydrogen atmosphere at atmospheric pressure. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 4-[(5-propyl-1,3,4-oxadiazol-2-yl)methyl]aniline as pale-yellow crystals (3.74 g, yield 55%) from a fraction eluted with hexane-ethyl acetate (1:1-1:2, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 60-61° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-789f366bc6af404fbe963896bcba0838
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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