1-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetraazole → 3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)aniline

HRID 896544Notes

Reaction equation

HRID 896544 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([CH:13]=[CH2:14])[CH:10]=[C:9]([N+:15]([O-])=O)[CH:8]=2)=[N:5][N:4]=[N:3]1>CO.[OH-].[OH-].[Pd+2]>[CH2:13]([C:11]1[CH:10]=[C:9]([CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH:12]=1)[NH2:15])[CH3:14]

Participants

4

Reactant 1

HCID 222526911-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetraazole

Product 1

HCID 222526943-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)anilineYield 95.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of impure 1-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetrazole (17.0 g) and palladium hydroxide on charcoal (3.0 g) in methanol (50 mL) was shaken under a hydrogen atmosphere (50 psig) for 4 hours. The mixture was filtered and the filtrate was concentrated under vacuum to provide an amber solid (14.3 g). 1H NMR (300 MHz, CDCl3) δ6.90 (s, 1H), 6.87 (s, 1H), 6.73 (s, 1H), 4.16 (s, 3H), 3.95 (bs, 2H), 2.65 (q, J=7 Hz, 2H), 1.22 (t, J=7 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-cd81567541fc4690b99b89addc9b38df
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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