Phosphorus oxychloride → 3,5-Dichloro-benzofuro[3,2-c]isoquinoline

HRID 869426Notes

Reaction equation

HRID 869426 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:7]=3[N:8]=[C:9]2O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:7]=3[N:8]=[C:9]2[Cl:22])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785169623-Chloro-benzofuro[3,2-c]isoquinoline-5-ol

Product 1

HCID 867222733,5-Dichloro-benzofuro[3,2-c]isoquinoline

Procedure

A mixture of 19B (11.8 mmol) in POCl3 (20 mL) was refluxed for 2 hours. After reaction completed, POCl3 was evaporated under reduced pressure. The residue was added into crushed ice and stirred for 10 min. The solids were collected by filtration and dried to give 3.2 g of a crude product, which was dissolved in dichloromethane and purified by flash chromatography (petroleum ether 1:1) and concentrated to give a pure product M19 (3.1 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter reaction
  3. customPOCl3 was evaporated under reduced pressure
  4. additionThe residue was added
  5. custominto crushed ice
  6. filtrationThe solids were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-573149b925c84f3da98822107018f8eb
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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