1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole → 3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline

HRID 1855495Notes

Reaction equation

HRID 1855495 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[N:15][C:14]([CH3:17])=[N:13]1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[N:15][C:14]([CH3:17])=[N:13]1

Participants

3

Reactant 1

HCID 595777881-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

Product 1

HCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)anilineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Methoxy-4-nitro-phenyl)-3-methyl-1H-[1,2,4]triazole (77 mg, 0.33 mmol) was dissolved in methanol (5 mL). The flask was evacuated and flushed with nitrogen. This procedure was repeated two times. 10% Palladium on charcoal (8 mg) was added. The reaction was stirred at room temperature under an atmosphere of hydrogen over night, filtered and the filtrate was evaporated under reduced pressure to yield the title compound as a brown solid (67 mg, ca. 100%). MS ISP (m/e): 205.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.35 (s, 1H), 7.37 (d, 1H), 6.32-6.35 (m, 2H), 3.82 (s, 3H), 2.47 (s, 3H).

Workup

  1. customThe flask was evacuated
  2. customflushed with nitrogen
  3. addition10% Palladium on charcoal (8 mg) was added
  4. filtrationfiltered
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-953dcc033ca14fa78f4ee7e25f82198c
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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