Iodoethane → 1-Chloro-7-fluoro-4-ethoxyisoquinoline

HRID 1852222Notes

Reaction equation

HRID 1852222 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](I)[CH3:21]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13][CH2:20][CH3:21])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 717427161-Chloro-7-fluoroisoquinolin-4-OL

Product 1

HCID 866832671-Chloro-7-fluoro-4-ethoxyisoquinolineYield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloro-7-fluoroisoquinolin-4-ol (0.5 g, 2.53 mmol) in acetonitrile (10 ml) was added K2CO3 (700 mg, 5.06 mmol) followed by ethyl iodide (475 mg, 3.04 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-7-fluoro-4-ethoxyisoquinoline (400 mg 70%) as off-white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customto get crude compound
  7. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7a9115e8fdb0409d93bf4d00ba942886
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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