Water → HCID 21192427, compound

HRID 1067246Notes

Reaction equation

HRID 1067246 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[C:10](=O)[NH:9][CH:8]=1.O>CC#N>[Cl:3][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[C:7]([Cl:6])=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 21192453HCID 21192453, compound

Product 1

HCID 21192427HCID 21192427, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

POCl3 (46 μL, 0.50 mmol) was added to a stirred suspension of 4-chloro-7-(phenylsulfanyl)-1-(2H)-isoquinolone (120 mg, 0.42 mmol) in MeCN (2 mL) at 23° C., and the mixture was heated at reflux for 1.5 h which gave a clear solution. This cooled solution was poured into water (20 mL) and the mixture was extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (90:10) as eluant to give 1,4-dichloro-7-(phenylsulfanyl)isoquinoline (92 mg, 0.30 mmol) as an oil which solidified on standing.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h which
  3. customgave a clear solution
  4. extractionthe mixture was extracted with EtOAc (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-94b0b0b3a9c8464da9b2355e398849a7
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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