Iodoethane → 1-Chloro-4-ethoxyisoquinoline

HRID 2361615Notes

Reaction equation

HRID 2361615 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](I)[CH3:20]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:19][CH3:20])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 42818821-Chloro-4-hydroxyisoquinoline

Product 1

HCID 866832431-Chloro-4-ethoxyisoquinolineYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 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-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1).

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-15f4521e5f7845398c35243427a4e61e
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

Loading…