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 1803129Notes

Reaction equation

HRID 1803129 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

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-5ddfbb4700c54a49974f5d37cf75d967
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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