Hydrochloric Acid → 2-Ethynylquinoline

HRID 1844388Notes

Reaction equation

HRID 1844388 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CCCCCC.Cl>CO.ClCCl>[C:6]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)#[CH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5133862-((Trimethylsilyl)ethynyl)quinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 130817492-Ethynylquinoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-((Trimethylsilyl)ethynyl)quinoline (1.289 g, 5.72 mmol), and K2CO3 (0.792 g, 5.73 mmol) were dissolved in a mixture of methanol (3 mL) and dichloromethane (1.5 mL), followed by stirring at room temperature. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:4). When the reaction was completed, the pH of the reactant was adjusted to 10 by addition of an aqueous solution of 1 M HCl and extracted with dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The thus obtained filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:4, R.f: 0.3), to thereby obtain 2-ethynylquinoline (0.742 g, 85%) as brown oil.

Workup

  1. extractionextracted with dichloromethane
  2. customto thereby separate an organic layer
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationThe thus obtained filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (EtOAc/Hexane=1:4, R.f: 0.3)

Sources & evidence

ORD record
ord-2e6d49af0de94b8492f284139a7ac371
Source dataset
uspto-grants-2015_02
Patent number
US08946431B2

Reaction notes

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