Hydrochloric Acid → 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 346476

Reaction equation

HRID 346476 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:4]=1.Cl>C(O)C.[Pd]>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21069882(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride

Product 1

HCID 210698804-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride): Intermediate 1,4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile, (2.46 g, 13.13 mmol) was dissolved in hot ethanol (150 mL). Aqueous 1N HCl (15 mL) was added followed by 10% Pd/C (200 mg). The mixture was shaken under H2 (55 psi) for 4 h., then filtered through Celite and concentrated in vacuo. The remaining residue was partitioned between ethyl acetate and water. The aqueous layer was isolated and lyophilized to give the title compound as a white powder (2.96 g, 99% yield). 1H NMR (500 MHz, CD3OD) δ ppm: 9.51 (1H, s), 8.63 (1H, s), 7.85 (1H, dd, J=8.5, 5.8 Hz), 7.68 (1H, dd, J=8.8, 2.4 Hz), 7.49 (1H, td, J=8.3, 2.4 Hz), 4.20 (2H, s). LCMS (M+H) calcd for C9H10N4F: 193.08; found: 193.16.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe remaining residue was partitioned between ethyl acetate and water
  4. customThe aqueous layer was isolated

Sources & evidence

ORD record
ord-0cc37b0f01c14e7797475ffa60949e5f
Source dataset
uspto-grants-2007_02
Patent number
US07173022B2

Linked notes

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