Phosphorus oxychloride → 1-Chloro-3-(4-methoxyphenyl)isoquinoline

HRID 1006871Notes

Reaction equation

HRID 1006871 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11](=O)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 123280893-(4-methoxyphenyl)isoquinolin-1(2H)-one

Product 1

HCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinolineYield 96%

Conditions

Temperature
110 °C

Procedure

3-(4-Methoxyphenyl)isoquinolin-1-one (1.70 g) was added to phosphorus oxychloride (10 ml), and the resulting mixture was heated at 110° C. for 3 hr. The reaction mixture was evaporated, and to the resulting residue were added ethyl acetate and water. The resulting organic layer was washed with water, an aqueous solution of sodium bicarbonate and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a white powder (1.76 g, yield; 96%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionto the resulting residue were added ethyl acetate and water
  3. washThe resulting organic layer was washed with water
  4. dry with materialan aqueous solution of sodium bicarbonate and brine, and then dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-563277a30e924e9ea3e63dcd904d3370
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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