Potassium Carbonate → 6-Ethynylisoquinoline

HRID 598840Notes

Reaction equation

HRID 598840 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O.O>[C:4]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)#[CH:3]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 579505646-((Trimethylsilyl)ethynyl)isoquinoline

Product 1

HCID 579505416-EthynylisoquinolineYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-(trimethylsilyl)ethynyl)isoquinoline (2.2 g, 9.8 mmol) in 45 mL of MeOH was added potassium carbonate (2.7 g, 20 mmol). After 1 hour, the reaction mixture was diluted with 100 mL of EtOAc and 50 mL of water. The mixture was partitioned and the aqueous portion was extracted three times with 50 mL of EtOAc. The combined organic layers were washed with 100 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 30% EtOAc/hexanes) afforded 6-ethynylisoquinoline (1.3 g, 87% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ pp 9.25 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.65 (dd, J=1.2 Hz, 8.6 Hz, 1H), 7.62 (d, J=5.8 Hz, 1H), 3.26 (s, 1H).

Workup

  1. customThe mixture was partitioned
  2. extractionthe aqueous portion was extracted three times with 50 mL of EtOAc
  3. washThe combined organic layers were washed with 100 mL of brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-8e18e16dd8e347b98fd2138a50f09876
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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