2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrobenzonitrile → 5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1803129

Reaktionsgleichung

Reaktionsgleichung von HRID 1803129
[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:8]=2[C:9]#[N:10])[N:3]=1>[Pd].CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:7]([N:4]2[CH:5]=[N:6][C:2]([CH3:1])=[N:3]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Komponenten

4

Edukt 1

HCID 668583402-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrobenzonitrile

Produkt 1

HCID 668600535-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrileAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Step G (2): 10% Palladium on carbon (5.06 g) was added under an atmosphere of nitrogen to a chilled (ice-water bath) solution of 2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrobenzonitrile (10.9 g, 47.6 mmol) dissolved in methanol (100 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 16 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 5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile (6.59 g, 70% yield) as a brown solid. LC-MS (M+H)+ 200.0. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.29-2.37 (m, 3 H) 5.99 (s, 2 H) 6.94 (dd, J=8.85, 2.44 Hz, 1 H) 7.00 (d, J=2.44 Hz, 1 H) 7.37 (d, J=8.54 Hz, 1 H) 8.69-8.81 (m, 1 H).

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-5ddfbb4700c54a49974f5d37cf75d967
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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