1-(3-Nitrophenyl)-1H-tetrazole → 3-(1H-1,2,3,4-tetrazol-1-yl)aniline

HRID 1809149Notes

Reaction equation

HRID 1809149 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 8273051-(3-Nitrophenyl)-1H-tetrazole

Product 1

HCID 8630073-(1H-1,2,3,4-tetrazol-1-yl)anilineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2 L pressure vessel was added 1-(3-nitrophenyl)-1H-tetrazole 10 (10.0 g, 52.3 mmol, 1.0 eq.) and methanol (500 mL). The resulting solution was purged with N2 for 5 min. 10% Pd/C (500 mg) was added to the solution and the vessel was placed on a Parr hydrogenator at 50 psi for 3 h. The Pd/C was removed by filtration and the filtrate was concentrated to yield a light gray solid (7.66 g, 91%). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 162.1 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d) δ 9.96 (s, 1H), 7.23-7.19 (m, 1H), 7.01-7.00 (m, 1H), 6.93-6.91 (m, 1H), 6.70-6.67 (m, 1H), 5.64 (m, 2H) ppm.

Workup

  1. customThe resulting solution was purged with N2 for 5 min
  2. addition10% Pd/C (500 mg) was added to the solution
  3. customThe Pd/C was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dc235e6540534322b95542f0a7fef3da
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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