Sulfuric Acid → HCID 66598088, compound

HRID 1038597Notes

Reaction equation

HRID 1038597 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][C:7](C#N)=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1.[CH3:13][Li].S(=O)(=O)(O)O.[C:20](=[O:23])([O-])O.[Na+]>O1CCCC1>[O:1]1[C:10]2[C:5](=[N:6][C:7]([C:20](=[O:23])[CH3:13])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 66599153HCID 66599153, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 66598088HCID 66598088, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-6-carbonitrile (16 mg, 99 μmol) was dissolved in tetrahydrofuran (500 μL), added methyllithium (150 μL (1.04 M in THF solution), 148 μmol) under ice-cold conditions, and the mixture was stirred at the same temperature for 5 minutes. The reaction solution was added 1M-sulfuric acid (2.0 mL), and stirred at room temperature for 3 hours. Under ice-cold conditions, the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate (pH=8 was confirmed). The reaction solution was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (8.3 mg (yield 47%)) was obtained as a yellow oil.

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-46805f99510346e49d41c84f9799f2c5
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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