1H-1,2,4-Triazole → 4-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehyde

HRID 388364Notes

Reaction equation

HRID 388364 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.F[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[CH:9][CH:8]=1>CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]=[O:18])=[CH:9][CH:8]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 70225244-Fluoronaphthalene-1-carbaldehyde

Product 1

HCID 866581554-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehydeYield 68.8%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

1,2,4-triazole (248 mg) is added to a solution of 4-fluoro-naphthalene-1-carbaldehyde (522 mg) and potassium carbonate (4 mg) in DMF (4 ml): After 3 hours a room temperature, the reaction is quenched with water (40 ml) and ethyl acetate (50 ml). The organic phase is separated and the aqueous phase is extracted two times with ethyl acetate. The organic phases are combined, extracted with water and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 4-[1,2,4]triazol-1-yl-naphthalene-1-carbaldehyde (460 mg) as beige crystals. MS (HPLC/MS): 224 (MH+). Retention time: 2.97 min.

Workup

  1. customthe reaction is quenched with water (40 ml) and ethyl acetate (50 ml)
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted two times with ethyl acetate
  4. extractionextracted with water and with a saturated aqueous solution of NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-8b0212816bb34f8a86a55ec82397fc7b
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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