Ethyl Acetate → 3-Chloro-6-ethynylisoquinoline

HRID 523063Notes

Reaction equation

HRID 523063 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:18]#[C:19][Si](C)(C)C)=[CH:13][CH:12]=2.C(OCC)(=O)C>CO>[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:18]#[CH:19])=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 899957303-Chloro-6-((trimethylsilyl)ethynyl)isoquinoline

Product 1

HCID 899955703-Chloro-6-ethynylisoquinolineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (9 mg, 0.0654 mmol) was added to a solution of 3-chloro-6-((trimethylsilyl)ethynyl)isoquinoline (Preparation 51, 170 mg, 0.654 mmol) in methanol (1 mL) and the reaction was stirred for 1 hour. Ethyl acetate (20 mL) was added and the organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 50% hexane in dichloromethane to afford the title compound as a white powder (110 mg, 90%).

Workup

  1. washthe organic solution was washed with water (20 mL), brine (20 mL)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with 50% hexane in dichloromethane

Sources & evidence

ORD record
ord-4b51848b615c4435928f4cbdc5c948ae
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

Loading…