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 451006

Reaction equation

HRID 451006 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>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[N:15][C:14]([CH3:17])=[N:13]1)[NH2:9]

Participants

4

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 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (1.2 g) was added under an atmosphere of nitrogen to a chilled (ice-water bath) solution of 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (3.7 g, 12.7 mmol) dissolved in methanol (250 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 18 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short diatomaceous earth (Celite®) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (2.44 g, 94% yield) as a reddish solid. LC-MS (M+H)+205.2. 1H NMR (500 MHz, CDCl3) δ ppm 8.35 (s, 1H) 7.36 (d, J=8.55 Hz, 1H) 6.29-6.34 (m, 2H) 3.80 (s, 3H) 2.46 (s, 3H).

Workup

  1. customThe flask was repeated evacuated
  2. customflushed with hydrogen gas (double balloon)
  3. waitleft
  4. customPurged with nitrogen gas
  5. filtrationFiltered the crude
  6. customreaction mixture through a short diatomaceous earth (Celite®) plug
  7. washRinsed
  8. customreaction vessel and plug with methanol

Sources & evidence

ORD record
ord-f6741d912f834eadac2f1e2cd6d6f75b
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Linked notes

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