5-(3-nitrophenyl)tetrazole → HCID 178507542, compound

HRID 963508Notes

Reaction equation

HRID 963508 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2851295-(3-nitrophenyl)tetrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 178507542HCID 178507542, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(3-Nitrophenyl)-1H-tetrazole (4.41 g) was hydrogenated in ethanol (50 ml) over 10% palladium on carbon (0.4 g) under 3 atmospheric pressure of hydrogen at ambient temperature. The reaction mixture was filtered through Celite® (Johns Manville) and washed with ethanol. The filtrate and the washings were combined and evaporated to give 5-(3-aminophenyl)-1H-tetrazole as a crystalline powder, which was triturated in diisopropyl ether and collected by filtration to afford the desired product as a white powder (3.19 g, 85.8%). This was used in a following reaction without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (Johns Manville)
  2. washwashed with ethanol
  3. customevaporated

Sources & evidence

ORD record
ord-8378aeccf8f84e9b87afc882ab018903
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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