Hydrochloric Acid → (4-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride

HRID 1664146Notes

Reaction equation

HRID 1664146 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[C:14]([CH3:15])=[N:13][CH:12]=[N:11]2)[CH:3]=1.[ClH:16].[H][H]>CCO.[Pd]>[ClH:16].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([N:10]2[C:14]([CH3:15])=[N:13][CH:12]=[N:11]2)[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 210699064-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 21069907(4-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile (2.9 g, 14 mmol) in EtOH (100 mL) was mixed with 1N—HCl (15 mL) and 10% Pd—C (0.7 g, Aldrich). This mixture was hydrogenated in a Parr shaker at 45-55 psi of hydrogen for 20 h. The catalyst was filtered over Celite®, and washed with EtOH. The filtrate was concentrated, and the residue triturated with EtOH-Et2O to obtain 3.17 g (13 mmol, 91% yield) of the title compound as an off-white powder: HPLC 0.47 min (AP 100% at 254 nm); LC/MS m/z 207 (M+H); 1H NMR (DMSO-d6, 300 MHz) δ ppm 2.40 (3H, s, CH3), 3.77 (2H, d, J=5.5 Hz, NCH2), 7.52-7.62 (1H, m), 7.66 (1H, dd, J=9.2, 2.6 Hz), 7.87 (1H, t, J=7 Hz), 8.14 (1H, s), 8.47 (3H, brs, NH3+).

Workup

  1. filtrationThe catalyst was filtered over Celite®
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated
  4. customthe residue triturated with EtOH-Et2O

Sources & evidence

ORD record
ord-9f8f9593432d4011a876e02d7d86c391
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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