Phosphorus oxychloride → 1-Chloro-7-methoxy-3-(2-methoxyphenyl)isoquinoline

HRID 1251148Notes

Reaction equation

HRID 1251148 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[N+:9]([O-])=[CH:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225035447-Methoxy-3-(2-methoxyphenyl)isoquinoline-2-oxide

Product 1

HCID 225036211-Chloro-7-methoxy-3-(2-methoxyphenyl)isoquinoline

Procedure

7-Methoxy-3-(2-methoxyphenyl)isoquinoline-2-oxide (0.60 g) and phosphorus oxychloride (5 ml) were reacted at 110° C. for 2 hr. The reaction solution was concentrated, and to the resulting residue were added ethyl acetate and an aqueous saturated sodium bicarbonate. The resulting organic layer was washed with water and brine, and 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 0.56 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the resulting residue were added ethyl acetate
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried 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-21aa46679e874c0dae716cf17dd51eb8
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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