Water → HCID 66599153, compound

HRID 1038596Notes

Reaction equation

HRID 1038596 reaction equation
[O:1]1[C:10]2[C:5](=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1.[CH2:12]([N:14](CC)CC)C.O>C(#N)C>[O:1]1[C:10]2[C:5](=[N:6][C:7]([C:12]#[N:14])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 66598282HCID 66598282, compound

Product 1

HCID 66599153HCID 66599153, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 5-oxide (102 mg, 666 μmol) was dissolved in actonitrile (700 μL), added triethylamine (202 mg, 2.00 mmol) and trimethylsilylnitrile (529 mg, 5.33 mmol) at room temperature, and the mixture was stirred at 100° C. overnight. Under ice-cold conditions, water was added, and 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 (chloroform/methanol), and the title compound (105 mg (yield 97%)) was obtained as a brown solid.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-0fc86d2f167d4647a16c9727f9eadb45
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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