Triethylamine → 3-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-YL)aniline

HRID 1855498Notes

Reaction equation

HRID 1855498 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[N:14][C:13]([CH3:16])=[N:12]1.C(N(CC)CC)C.[H][H]>O1CCCC1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[N:14][C:13]([CH3:16])=[N:12]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 575269631-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 575269743-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-YL)anilineYield 73.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Fluoro-4-nitro-phenyl)-3-methyl-1H-[1,2,4]triazole (250 mg, 1.13 mmol) was dissolved in tetrahydrofurane (6 mL) and triethylamine (5 mL) and stirred for 2 hours with 10% palladium on carbon (55 mg) under 1.5 bar of hydrogen. The reaction mixture was filtered and the solvent was removed under reduced pressure to yield the title compound (159 mg, 73%) as a yellow solid MS ISP (m/e): 193.3 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.31 (d, 1H), 7.45 (dd, 1H), 6.51 (m, 2H), 3.94 (s broad, 2H), 2.48 (s, 3H). Mp 122-125° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a0079d5d79e346e9b9b0fc708fbc4841
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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