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

HRID 896515Notes

Reaction equation

HRID 896515 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(OCC)(=O)C.CO.[Pd]>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)=[N:5][N:4]=[N:3]1

Participants

5

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 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Methyl-5-(3-nitrophenyl)-tetrazole (28.8 g, 140 mmol) was dissolved in ethyl acetate (430 mL) and methanol (1270 mL). Palladium on carbon (2.7 g, 10 wt %) was added and the mixture was shaken under a hydrogen atmosphere (60 psig) for 1.5 hours. The mixture was filtered, and the filtrate was concentrated under vacuum to give a white solid (24.0 g, 98%) which was used without further purification. 1H NMR (300 MHz, CDCl3), δ7.21 (dd, J=8, 7 Hz, 1H), 6.99 (s, 1H), 6.90 (d, J=7 Hz, 1H), 6.76 (d, J=8 Hz, 1H), 5.44 (bs, 2H), 4.10 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b6e2c63d620b452eb68ce31aebd5ddc4
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

Loading…