Methanol → HCID 86748468, compound

HRID 275027Notes

Reaction equation

HRID 275027 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)=C[CH:4]=1.[C:15](=[O:18])(O)[O-:16].[Na+].[CH3:20]O>>[C:10]1([C:15]([O:16][CH3:20])=[O:18])[NH:9][CH:8]=[CH:7][C:6]2[C:11]=1[CH:12]=[CH:3][CH:4]=2

Participants

4

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 19077342HCID 19077342, compound

Product 1

HCID 86748468HCID 86748468, 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-6d2c4ae8a3f3435b902a9a981b93ee4e
Source dataset
uspto-grants-1995_02
Patent number
US05391743

Reaction notes

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