Diethyl Ether → 1,4-Dichloroisoquinoline-7-sulfonyl chloride

HRID 2289806Notes

Reaction equation

HRID 2289806 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH:14][CH:15]=2)[C:10](=O)[NH:9][CH:8]=1.CCOCC>CC#N>[Cl:3][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:17]([Cl:20])(=[O:19])=[O:18])[CH:12]=2)[C:7]([Cl:6])=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24813Phosphorus oxychlorideHCID 166583514-Chloro-1-hydroxy-7-isoquinolinesulfonyl chloride

Product 1

HCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Anal. Found: C, 39.37; H, 2.09; N, 4.94. Calc for C9H5Cl2NO3S: C, 38.87; H, 1.81; N, 5.04. ##STR109## POCl3 (9.65 mL, 103.5 mmol) was added to a stirred suspension of 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinesulphonyl chloride (22.1 g, 79.6 mmol) in MeCN (500 mL) at room temperature and the mixture was then heated at reflux for 15 h. On cooling, the MeCN solution was decanted from the insoluble sludge and evaporated in vacuo. The residue was extracted with hot EtOAc and evaporated to leave a solid which was stirred with Et2O (1.2 L) at room temperature overnight. The ethereal solution was decanted from the insoluble material and evaporated in vacuo to give 1,4-dichloro-7-isoquinolinesulphonyl chloride (20 g, 67 mmol) as a pale yellow solid.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 15 h
  3. temperatureOn cooling
  4. customthe MeCN solution was decanted from the insoluble sludge
  5. customevaporated in vacuo
  6. extractionThe residue was extracted with hot EtOAc
  7. customevaporated
  8. customto leave a solid which
  9. customThe ethereal solution was decanted from the insoluble material
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-b394c4b6b492457f97d5f33705cb6977
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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