Phosphorus oxychloride → 1627603-62-6

HRID 1476803Notes

Reaction equation

HRID 1476803 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N+:6]=1[O-])=[O:4].O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:7]1[N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90387073HCID 90387073, compound

Product 1

HCID 903869511627603-62-6Yield 49%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(methoxycarbonyl)isoquinoline 2-oxide (9.5 g, 46.75 mmol) and POCl3 (50 mL) was heated at 100° C. for 4 hours. The reaction mixture was subsequently cooled and concentrated, and the crude product was purified by silica gel chromatography eluting with petroleum ether and EtOAc (15:1) to give the title compound as a white solid (5.1 g, 49%). ESI-MS m/z [M+H]+ 222.

Workup

  1. temperatureThe reaction mixture was subsequently cooled
  2. concentrationconcentrated
  3. customthe crude product was purified by silica gel chromatography
  4. washeluting with petroleum ether and EtOAc (15:1)

Sources & evidence

ORD record
ord-8793b6b23f3549eb88096d3f35950c58
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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