4-Hydroxybenzaldehyde → HCID 17859705, compound

HRID 347675Notes

Reaction equation

HRID 347675 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 17859705HCID 17859705, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,6-Dichloropyridazine (3.00 g, 20.1 mmol), 4-hydroxybenzaldehyde (2.46 g, 20.1 mmol), potassium carbonate (2.78 g, 20.1 mmol) and 60 mL of N,N-dimethylformamide were mixed and the mixture was refluxed for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The extracted solution was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v) to obtain 4.06 g (86%) of the title compound as colorless crystalline powder.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe extracted solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v)

Sources & evidence

ORD record
ord-3b8cfaeaaf8c4c44af8c190641179feb
Source dataset
uspto-grants-2007_02
Patent number
US07176204B2

Reaction notes

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