Hydrochloric Acid → 7-Methoxyisoquinoline

HRID 275023

Reaction equation

HRID 275023 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)S(C1C=CC(C)=CC=1)(=O)=O)C.O1CCOCC1.Cl>O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]2[C:23]([CH:4]=[CH:5][N:6]=[CH:17]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 19077332N-(2,2-diethoxyethyl)-N-[(3-methoxyphenyl)methyl]-4-methyl-benzenesulfonamide

Product 1

HCID 5943757-MethoxyisoquinolineYield 102.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2 liter round bottom flask equipped with a magnetic stir bar, condenser and nitrogen inlet is added (75 g, 0.184 mole) of N-(2,2-diethoxyethyl)-N-[(3-methoxyphenyl)methyl]-4-methyl-benzenesulfonamide, 1.0 liter of dioxane and 200 ml of 6N HCl. This slurry is stirred and heated at reflux under nitrogen for 18 hours. The reaction solution is then slowly poured into 1 liter of H2O and stirred for an additional 30 minutes then extracted with ether (2×500 ml). The pH of the aqueous layer is adjusted to 8 with ammonium hydroxide, the product is extracted with dichloromethane. The combined organics extracts are dried over MgSO4, filtered and evaporated to yield 30 g of an oil. The crude product is purified by chromatography with 12.0% acetone in dichloromethane to provide the product (19.7 g) in a 67% yield.

Workup

  1. customTo a 2 liter round bottom flask equipped with a magnetic stir bar, condenser and nitrogen inlet
  2. temperatureheated
  3. temperatureat reflux under nitrogen for 18 hours
  4. stirringstirred for an additional 30 minutes
  5. extractionthen extracted with ether (2×500 ml)
  6. extractionthe product is extracted with dichloromethane
  7. dry with materialThe combined organics extracts are dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ff8ecbff566d4c53b4a02cacd79349c0
Source dataset
uspto-grants-1995_02
Patent number
US05391743

Linked notes

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