5-Methyl-3-(4-nitrobenzyl)-1,2,4-oxadiazole → HCID 69209127, compound

HRID 30664Notes

Reaction equation

HRID 30664 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[N:3]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].O1CCCC1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[N:3]=1

Participants

4

Reactant 1

HCID 28090665-Methyl-3-(4-nitrobenzyl)-1,2,4-oxadiazole

Product 1

HCID 69209127HCID 69209127, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-methyl-3-(4-nitrobenzyl)-1,2,4-oxadiazole (3.89 g), Lindlar catalyst (2.0 g) and tetrahydrofuran (200 mL) was 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-methyl-1,2,4-oxadiazol-3-yl)methyl]aniline as a brown oil (0.33 g, yield 10%) from a fraction eluted with hexane-ethyl acetate (3:1-2:1, v/v).

Workup

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

Sources & evidence

ORD record
ord-518c5b8056a54d8c907a486eed2cdd63
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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