Phosphorus oxychloride → 1,7-Dichloroisoquinoline-3-carbonitrile

HRID 1476819Notes

Reaction equation

HRID 1476819 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]([NH2:15])=O)[NH:8][C:9]2=O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([C:13]#[N:15])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 903871057-Chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

Product 1

HCID 846880831,7-Dichloroisoquinoline-3-carbonitrileYield 81.8%

Procedure

A solution of 7-chloro-1-oxo-1,2-dihydroisoquinoline-3-carboxamide (550 mg, 2.46 mmol) in POCl3(10 mL) was heated to reflux for 6 hours. The solvent was subsequently removed in vacuo and the crude product was purified by column chromatography eluting with petroleum ether and ethyl acetate (PE/EA=30:1) to give the title compound (450 mg, 81.8%). 1H NMR (400 MHz, CDCl3) δ ppm 8.35 (d, J=1.6 Hz, 1H), 8.02 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.80 (dd, J=1.6 Hz and 8.0 Hz, 1H).

Workup

  1. temperatureto reflux for 6 hours
  2. customThe solvent was subsequently removed in vacuo
  3. customthe crude product was purified by column chromatography
  4. washeluting with petroleum ether and ethyl acetate (PE/EA=30:1)

Sources & evidence

ORD record
ord-7ba3de1e37b84601ae04ad12c49fd6d0
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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