Hydrochloric Acid → (4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride

HRID 348140Notes

Reaction equation

HRID 348140 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:3]=1.[ClH:15]>C(O)C.[Pd]>[ClH:15].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 210698804-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

Product 1

HCID 21069882(4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 67, 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile, (2.46 g, 13.13 mmol) was dissolved in hot ethanol (150 mL). To this was added 1N HCl (15 mL) followed by 10% Pd—C (200 mg). The mixture was treated with H2 at 55 psi for 4 h in a Parr shaker then filtered over Celite and the solvent removed under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The aqueous phase was separated and lyophilized to afford 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. additionThe mixture was treated with H2 at 55 psi for 4 h in a Parr shaker
  2. filtrationthen filtered over Celite
  3. customthe solvent removed under reduced pressure
  4. customThe resulting residue was partitioned between ethyl acetate and water
  5. customThe aqueous phase was separated

Sources & evidence

ORD record
ord-a32e6bcf0e1246bd8f28e1f64c56ddc1
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

Loading…