2-Methyl-5-(3-nitrophenyl)-2H-tetrazole → 3-(2-Methyl-2H-tetrazol-5-yl)aniline

HRID 2379347Notes

Reaction equation

HRID 2379347 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:3]1>C(O)C.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([C:4]2[N:5]=[N:6][N:2]([CH3:1])[N:3]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 140450862-Methyl-5-(3-nitrophenyl)-2H-tetrazole

Product 1

HCID 144421273-(2-Methyl-2H-tetrazol-5-yl)anilineYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-5-(3-nitrophenyl)tetrazole (2.30 g, 0.0112 mol) was hydrogenated at 20 psi in ethanol (50 ml) using 10% palladium on carbon (230 mg) for 15 min. The mixture was filtered then evaporated to dryness in vacuo to give the title compound (1.55 g, 79%) as a colourless solid. mp 97° C. Rf 0.40 in dichloromethane:methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ 3.80 (2H, brs), 4.38 (3H, s), 6.78 (1H, ddd, J=8, 2 and 2 Hz), 7.26 (1H, dd, J=8 and 8 Hz), 7.47 (1H, dd, J=2 and 2 Hz), 7.51 (1H, dd, J=8 and 2 Hz).

Workup

  1. customfor 15 min
  2. filtrationThe mixture was filtered
  3. customthen evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-61e207a9edcc41b794b80e7bfc779355
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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