Phosphorus oxychloride → 1,8-Dichloroisoquinoline-3-carbonitrile

HRID 1476825Notes

Reaction equation

HRID 1476825 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=O)[NH:9][C:8]([C:13]([NH2:15])=O)=[CH:7]2.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[Cl:1])[CH:7]=[C:8]([C:13]#[N:15])[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 903869708-Chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

Product 1

HCID 903870031,8-Dichloroisoquinoline-3-carbonitrileYield 40%

Procedure

A solution of 8-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide (0.5 g, 1.99 mmol) in POCl3 (10 mL) was heated to reflux for 4 hours. The reaction mixture was subsequently concentrated in vacuo and the crude product was purified by column chromatography eluting with petroleum ether and ethyl acetate (PE/EtOAc=5:1-2:1 gradient) to give the title compound (200 mg, 40%). ESI-MS m/z [M+H]+ 223.1.

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationThe reaction mixture was subsequently concentrated in vacuo
  3. customthe crude product was purified by column chromatography
  4. washeluting with petroleum ether and ethyl acetate (PE/EtOAc=5:1-2:1 gradient)

Sources & evidence

ORD record
ord-ba1abfbe71204ee98be91f176988f666
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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