2-methyl-5-(4-nitrophenyl)-2H-tetrazole → 4-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)aniline

HRID 1921793Notes

Reaction equation

HRID 1921793 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[N:3]1>[Pd].C(O)C>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[N:3]1

Participants

4

Reactant 1

HCID 3231922-methyl-5-(4-nitrophenyl)-2H-tetrazole

Product 1

HCID 11328464-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)anilineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-5-(4-nitro-phenyl)-2H-tetrazole (0.260 g, 1.27 mmol) and palladium on charcoal (53.6 mg) in ethanol (50 mL) is stirred in high pressure reactor under H2 at 4 bars for 17 hours. The catalyst is removed by filtration through Celite 521, washing with EtOH. The filtrates are combined and concentrated in vacuo to afford the title compound as a white solid (0.213 g, 96%). HPLC (254 nm) 1.50 min (89%)

Workup

  1. customThe catalyst is removed by filtration through Celite 521
  2. washwashing with EtOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-277e7eb90c854d81bdd6ff8fd2f6bb88
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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