Phosphorus oxychloride → HCID 86041352, compound

HRID 639879Notes

Reaction equation

HRID 639879 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])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([CH3:14])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11357571HCID 11357571, compound

Product 1

HCID 86041352HCID 86041352, compound

Procedure

A mixture of 6-methoxy-3-methyl-4-phenylisoquinolin-1(2H)-one (3.0 g) and 12 mL of POCl3 was heated to reflux for 1 h, then cooled to room temp and poured into ice. The mixture was extracted with EtOAc (3×). The combined organic solutions were washed with brine (1×) and saturated aqueous sodium carbonate (1×), then dried (Na2SO4) and concentrated. Flash chromatography (10% EtOAc/hexanes) gave 2.6 g of 1-chloro6-methoxy-3-methyl-4-phenylisoquinoline.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. additionpoured into ice
  4. extractionThe mixture was extracted with EtOAc (3×)
  5. washThe combined organic solutions were washed with brine (1×) and saturated aqueous sodium carbonate (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9a6cf7aeed24090bd5927532aaa51b2
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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