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

HRID 1766386Notes

Reaction equation

HRID 1766386 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-9f30dec623a1462bbf5128529a576630
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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