Phosphorus oxychloride → 1-Chloro-6-methoxy-3-methylisoquinoline

HRID 1511472Notes

Reaction equation

HRID 1511472 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][C:7]([CH3:14])=[CH:6]2.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:14])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 123270606-Methoxy-3-methylisoquinolin-1(2H)-one

Product 1

HCID 578930951-Chloro-6-methoxy-3-methylisoquinoline

Procedure

The isoquinoline of step 2 was dissolved in phosphorus oxychloride (2.5 mL) and heated at reflux for 1 hour. The excess phosphorus oxychloride was removed under reduced pressure and the residue was dissolved in chloroform. The resulting solution was washed with 1N aq. sodium hydroxide, water and brine. Evaporation of the solvent under reduced pressure gave crude 1-chloro-6-methoxy-3-methylisoquinoline, which was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe excess phosphorus oxychloride was removed under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe resulting solution was washed with 1N aq. sodium hydroxide, water and brine
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-04e0c1e65adf462e83c139abb7ab8e91
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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