Selenium Dioxide → HCID 71186638, compound

HRID 705050Notes

Reaction equation

HRID 705050 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]2.[Se](=O)=[O:15]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[O:15]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12023321HCID 12023321, compound

Product 1

HCID 71186638HCID 71186638, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under argon, a mixture of 6-chloroisoquinoline-1,3(2H,4H)-dione (600 mg g, 3.0 mmol) and selenium dioxide (357 mg, 3.2 mmol) in abs. 1,4-dioxane (20 ml) was stirred at a temperature of 100° C. for 3 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Purification of the residue that remained by column chromatography (gradient ethyl acetate/n-heptane) gave 6-chloroisoquinoline-1,3,4(2H)-trione (169 mg, 22% of theory) in the form of a slightly yellowish solid. 1H-NMR (400 MHz, d6-DMSO δ, ppm) 12.02 (br. s, 1H, NH), 8.12 (d, 1H), 8.01-7.95 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customPurification of the residue

Sources & evidence

ORD record
ord-f9cde8d2c33f43d3ba4a90404fe1e4f2
Source dataset
uspto-grants-2015_11
Patent number
US09173395B2

Reaction notes

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