Hydrochloric Acid → HCID 86678200, compound

HRID 1747546Notes

Reaction equation

HRID 1747546 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:15]=[N:14][N:13]([CH3:16])[N:12]=2)=[N:9][CH:10]=1)C.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:16][N:13]1[N:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][N:9]=2)[CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86678199HCID 86678199, compound

Product 1

HCID 86678200HCID 86678200, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (6.5 mL) was dissolved 5-(diethoxymethyl)-2-(2-methyl-2H-1,2,3-triazol-4 yl)pyridine (672 mg, 2.56 mmol) obtained in Step 5. To the solution was added 1 mol/L hydrochloric acid (6.40 mL, 6.40 mmol) and the mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 7/3) to give 6-(2-methyl-2H-1,2,3-triazol-4-yl)nicotinaldehyde (473 mg, 98% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-15d67cdc7a3e4515aff887bf64d3a7cc
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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