Methanol → HCID 86748470, compound

HRID 964534Notes

Reaction equation

HRID 964534 reaction equation
[Cl-].O[C:3]1[C:12]([N+]#N)=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5]C=1.[C:15](=[O:18])(O)[O-:16].[Na+].[CH3:20]O>>[CH:10]1[NH:9][CH:8]=[CH:7][C:6]2[C:11]=1[C:12]([C:15]([O:16][CH3:20])=[O:18])=[CH:3][CH:5]=2

Participants

4

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 19077342HCID 19077342, compound

Product 1

HCID 86748470HCID 86748470, compoundYield 50%

Procedure

7-Hydroxy-8-isoquinolinediazonium chloride (0.50 g, 2.4 mmol) and sodium bicarbonate (302 mg, 3.6 mmol) in anhydrous methanol (650 ml) is irradiated with a 275 watt sunlamp at 0° C. for 3 hours. The reaction mixture is evaporated to dryness under vacuum. The crude residue is dissolved in water and the product is extracted in methylene chloride. The combined organic extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the product as an orange solid (210 mg) in 50% yield.

Workup

  1. customThe reaction mixture is evaporated to dryness under vacuum
  2. dissolutionThe crude residue is dissolved in water
  3. extractionthe product is extracted in methylene chloride
  4. dry with materialThe combined organic extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1509a2a8d30422884239694a09fd590
Source dataset
uspto-grants-1998_06
Patent number
US05770586

Reaction notes

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