Ethanol → 1-(4-aminobenzyl)-1H-tetrazole

HRID 30692Notes

Reaction equation

HRID 30692 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>[C].[Pd].O1CCCC1>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 103305751-(4-nitrobenzyl)-1H-tetrazole

Product 1

HCID 103749291-(4-aminobenzyl)-1H-tetrazoleYield 71%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-nitrobenzyl)-1H-tetrazole (5 g), 10% palladium carbon (500 mg), ethanol (100 ml) and tetrahydrofuran (100 ml) was stirred under a hydrogen atmosphere at room temperature for 4 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate-hexane gave 1-(4-aminobenzyl)-1H-tetrazole (3.03 g, 71%) as yellow prism crystals. melting point: 138-140° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-06197c02a3944c539be63416b077ea4a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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