Hydrochloric Acid → HCID 10443913, compound

HRID 1795128Notes

Reaction equation

HRID 1795128 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].Cl>CN(C)C=O>[CH2:18]([C:9]([CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([C:12]#[N:13])[C:10]#[N:11])[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 22185758HCID 22185758, compound

Product 1

HCID 10443913HCID 10443913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

((6-Chloro-3-pyridyl)methyl)malononitrile (58 mg) was dissolved in N,N-dimethylformamide (2 ml), and sodium hydride (60% in oil, 14 mg) was added to the solution with stirring under ice-cooling. Then allyl bromide (0.13 ml) was added dropwise thereto, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 10% hydrochloric acid, and extracted with diethyl ether. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 26 mg of 2-allyl-2-((6-Chloro-3-pyridyl)methyl)malononitrile represented by the following formula (hereinafter referred to as the present invention compound (1)).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed successively with 10% hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained

Sources & evidence

ORD record
ord-36a172b24cfe4146aec4e3f9d35dcec0
Source dataset
uspto-grants-2006_04
Patent number
US07026340B2

Reaction notes

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