3-Chloroisoquinoline → 3-Ethoxyisoquinoline

HRID 2405779Notes

Reaction equation

HRID 2405779 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[O-:12][CH2:13][CH3:14].[K+]>>[CH2:13]([O:12][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:14]

Participants

3

Reactant 2

HCID 6409683-ChloroisoquinolineHCID 23670592Potassium ethoxide

Product 1

HCID 6409663-EthoxyisoquinolineYield 48.1%

Conditions

Temperature
150 °C

Procedure

3-Chloroisoquinoline (3.0, 18 mmol) was dissolved in potassium ethoxide (24% in EtOH, 10.6 mL, 27 mmol) and heated to 150° C. in a sealed tube for 24 h. After cooling, the solvent was removed in vacuo and the residue treated with 1M HCl until the solution reaches a pH 3. Saturated NaHCO3 solution then added slowly to return the solution to pH 8 followed by extraction with CHCl3. The combined organics were washed with brine, dried over anhydrous MgSO4. The residue obtained from concentration in vacuo was purified by column chromatography on SiO2 (0-15% EtOAc, hex) to afford 1.5 g (48%) of 3-ethoxyisoquinoline. LCMS found 174.11 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. additionthe residue treated with 1M HCl until the solution
  4. additionSaturated NaHCO3 solution then added slowly
  5. extractionfollowed by extraction with CHCl3
  6. washThe combined organics were washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. customThe residue obtained from concentration in vacuo
  9. customwas purified by column chromatography on SiO2 (0-15% EtOAc, hex)

Sources & evidence

ORD record
ord-cef4d907a0fd4ddcb31109763f85a618
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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