Ethanol → 2-(4-aminobenzyl)-2H-tetrazole

HRID 30691Notes

Reaction equation

HRID 30691 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[N:13]=[N:12][CH: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[N:13]=[N:12][CH:11]=[N:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 103528962-(4-nitrobenzyl)-2H-tetrazole

Product 1

HCID 104422102-(4-aminobenzyl)-2H-tetrazoleYield 66.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-nitrobenzyl)-2H-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 2-(4-aminobenzyl)-2H-tetrazole (2.83 g, 66%) as yellow prism crystals. melting point: 86-87° 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-94bfac7222d046648e220fd55295a257
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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