Hydrochloric Acid → 5-Formylpyridine-2-carbonitrile

HRID 1186410Notes

Reaction equation

HRID 1186410 reaction equation
C[N:2]1[CH:7]=[C:6]([CH:8]2[O:12]CCO2)[CH:5]=[CH:4][C:3]1=O.[CH3:14][N:15]1C=CC=C(C2OCCO2)C1=O.Cl>O1CCCC1>[C:14]([C:3]1[N:2]=[CH:7][C:6]([CH:8]=[O:12])=[CH:5][CH:4]=1)#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10397411HCID 10397411, compoundHCID 10419796HCID 10419796, compound

Product 1

HCID 109862635-Formylpyridine-2-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 73:27 mixture (933 mg, 5.15 mmol) of 1-methyl-5-(1,3-dioxolan-2-yl)-2(1H)-pyridone and 1-methyl-3-(1,3-dioxolan-2-yl)-2(1H)-pyridone was dissolved in tetrahydrofuran (10.0 mL). To this, 1N hydrochloric acid (10.0 mL) was added under a nitrogen atmosphere at room temperature and the mixture was stirred at the same temperature for 12 hours. Then, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and thereby 6-cyano-3-pyridinecarboxaldehyde (364 mg, yield: 100%) was obtained. The residue was purified by preparative thin-layer chromatography (ethyl acetate) to give 1-methyl-5-formyl-2(1H)-pyridone (309 mg, yield: 45%).

Workup

  1. extractionThen, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate
  2. washby washing with brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-8f1517e2328b48298cf899ea0fc2f43b
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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