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 475715

Reaktionsgleichung

Reaktionsgleichung von HRID 475715
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 595778183-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)anilineAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a23154dc9257412eae402184617fad35
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637525B2

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