Hydrochloric Acid → (4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochloride

HRID 62066Notes

Reaction equation

HRID 62066 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[ClH:25]>C(O)C.[Pd]>[ClH:25].[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669571074-[1-(4-Trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile

Product 1

HCID 118675148(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochlorideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL flask, 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzonitrile (3.00 g, 9.09 mmol) in ethanol (30 mL) was taken and hydrogen chloride (12 N, 3 mL) was added followed by palladium on carbon (10 wt %, 0.500 g). The reaction mixture was evacuated and purged with hydrogen gas. The reaction mixture was stirred under hydrogen (50 psi) for 24 hours. The reaction mixture was filtered over Celite®, concentrated and the solid obtained triturated with diethyl ether to give the title compound as an off-white solid (2.80 g, 93%): mp 259-263° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.43 (s, 1H), 8.37 (bs, 3H), 8.15 (d, J=8.1 Hz, 2H), 8.08 (d, J=9.3 Hz, 2H), 7.63 (d, J=8.1 Hz, 4H), 4.10 (q, J=6.0 Hz, 2H); ES+ m/z 335 ([M+H]+).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen gas
  3. filtrationThe reaction mixture was filtered over Celite®
  4. concentrationconcentrated
  5. customthe solid obtained
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-71ee8230f2324e7fa7d8d36dfb917e01
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Reaction notes

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