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

HRID 1592345Notes

Reaction equation

HRID 1592345 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 887MethanolSolvent2×

Procedure

Pd(OH)2(3.0 g) was carefully wetted down under nitrogen with methanol then 1-methyl-5-(3-nitro-5-vinylphenyl)-1H-tetraazole (17.0 g) dissolved in 50 ml of methanol was added. Hydrogenated at 50 PSI for 4 hours. Worked up by filtering the reaction under nitrogen through fiberglass filter paper. The filtrate was stripped in vacuo to give 14.3 g of amber solids as product. NMR (300 MHz, CDCl3) δ 6.90 (s, 1H), 6.87 (s, 1H), 6.73 (s, 1H), 4.16 (s, 3H), 3.95 (bs, 2H), 2.65 (q, 2H, J=7 Hz), 1.22 (t, 3H, J=7 Hz).

Workup

  1. additionwas added
  2. filtrationby filtering
  3. customthe reaction under nitrogen through fiberglass
  4. filtrationfilter paper

Sources & evidence

ORD record
ord-358c715e09f64d93a9766d20233bda71
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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