Triethylamine → 3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)aniline

HRID 1855500Notes

Reaction equation

HRID 1855500 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[C:15]([CH3:16])=[N:14][CH:13]=[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[C:15]([CH3:16])=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 584144611-(2-fluoro-4-nitrophenyl)-5-methyl-1H-1,2,4-triazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 584144593-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)anilineYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Fluoro-4-nitro-phenyl)-5-methyl-1H-[1,2,4]triazole (120 mg, 0.54 mmol) was dissolved in tetrahydrofurane (6 mL) and triethylamine (10 mL) and stirred for 4 hours with 10% palladium on carbon (50 mg) under 3 bar of hydrogen. The reaction mixture was filtered and the solvent was removed in vacuo to yield the title compound (78 mg, 75%) as a yellow solid. MS ISP (m/e): 193.3 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.93 (s, 1H), 7.16 (dd, 1H), 6.51 (m, 2H), 4.03 (s broad, 2H), 2.38 (s, 3H). Mp 106-108° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f1ac76d4783043c19055963b4241e8a4
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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