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

HRID 1939163Notes

Reaction equation

HRID 1939163 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 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-5-(3-nitrophenyl)tetrazole (2.30 g) was hydrogenated at 20 psi in ethanol (50 ml) using 10% palladium on carbon (230 mg) for 15 minutes. The mixture was filtered then evaporated to dryness in vacuo to give the title compound as a colourless solid (1.55 g), mp 97° C. Rf 0.40 in dichloromethane/methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ3.80 (2H, broad resonance), 4.38 (3H, s), 6.78 (1H, ddd, J1 =J2 =8 Hz, J3 =8 Hz), 7.26 (1H, dd, J1 =J2 =8 Hz), 7.47 (1H, dd, J1 =J2 =2 Hz), 7.51 (1H, dd, J1 =2 Hz, J2 =8 Hz).

Workup

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

Sources & evidence

ORD record
ord-69aeb972f7734bcd82f3b953ac040678
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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