1-methyl-5-(3-nitrophenyl)-1H-Tetrazole → 3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

HRID 1939164Notes

Reaction equation

HRID 1939164 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:5][N:4]=[N:3]1>C(O)C.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 140450781-methyl-5-(3-nitrophenyl)-1H-Tetrazole

Product 1

HCID 144576753-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)anilineYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-5-(3-nitrophenyl)tetrazole (Example 13, 350 mg) was hydrogenated at 20 psi in ethanol (30 ml) using 10% palladium on carbon (35 mg) for 15 minutes. The mixture was filtered then evaporated to dryness in vacuo to give the title compound as a grey solid (220 mg), mp 156°-157° C. Rf 0.23 in dichloromethane/methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ3.92 (2H, broad resonance), 4.16 (3H, s), 6.86 (1H, ddd, J1 =J2 =2 Hz, J3 =8 Hz), 7.01 (1H, broad d, J=8 Hz), 7.06 (1H, dd, J1 =J2 =2 Hz), 7.32 (1H, dd, J1 =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-e57cd067ee7041e0b7ece6cc73c4bed4
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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