Phosphorus oxychloride → 1-Chloro-8-methoxyisoquinoline-3-carbonitrile

HRID 1476832Notes

Reaction equation

HRID 1476832 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[NH:10][C:9]([C:14]([NH2:16])=O)=[CH:8]2.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[O:2][CH3:1])[CH:8]=[C:9]([C:14]#[N:16])[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 903870378-Methoxy-1-oxo-1,2-dihydroisoquinoline-3-carboxamide

Product 1

HCID 903871861-Chloro-8-methoxyisoquinoline-3-carbonitrileYield 82%

Procedure

A solution of 8-methoxy-1-oxo-1,2-dihydroisoquinoline-3-carboxamide (800 mg, 3.66 mmol) in POCl3(40 mL) was heated to reflux for 1 hour. The reaction mixture was subsequently concentrated in vacuo to give the title compound (660 mg, 82%). 1H NMR (400 MHz, CDCl3) δ ppm 7.98 (s, 1H), 7.78 (t, 1H, J=8.0 Hz), 7.48 (d, 1H, J=8.0 Hz), 7.20 (d, 1H, J=8.0 Hz), 4.05 (s, 3H); ESI-MS m/z [M+H]+ 219.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationThe reaction mixture was subsequently concentrated in vacuo

Sources & evidence

ORD record
ord-bec369d5c1184af98365631722914167
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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