Ethanol → HCID 20140046, compound

HRID 1252477Notes

Reaction equation

HRID 1252477 reaction equation
[CH:1]1[C:10]2C=CC[C:6](=O)[C:5]=2C=C[N:2]=1.[NH2:12]O.[CH2:14]([OH:16])C.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH:2]1[C:1]2[C:20]3[CH:19]=[CH:18][N:17]=[CH:22][C:21]=3[CH2:6][CH2:5][C:10]=2[NH:12][C:14]1=[O:16]

Participants

5

Reactant 4

HCID 702EthanolHCID 787HydroxylamineHCID 1049PyridineHCID 14276097HCID 14276097, compound

Product 1

HCID 20140046HCID 20140046, compoundYield 61.7%

Procedure

Isoquinolin-5-one (21.57 g, 0.147M) and hydroxylamine (15.55 g, 0.22M) together with approximately 300 ml of dry ethanol and 75 ml of pyridine was stirred at reflux temperature of the mixture for 6 hours. The solvent was then removed by evaporation and the residue was dissolved in a mixture of diethyl ether and water (600 ml, ca. 1:1). The organic phase was separated and extracted with water to remove residual pyridine, washed with saturated, aqueous solution of sodium chloride and dried over magnesium sulfate crystals. The inorganic matter was removed by filtration and the solvent by evaporation leaving 14.7 grams of the desired product (61.7% yield).

Workup

  1. temperatureat reflux temperature of the mixture for 6 hours
  2. customThe solvent was then removed by evaporation
  3. dissolutionthe residue was dissolved in a mixture of diethyl ether and water (600 ml, ca. 1:1)
  4. customThe organic phase was separated
  5. extractionextracted with water
  6. customto remove residual pyridine
  7. washwashed with saturated, aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate crystals
  9. customThe inorganic matter was removed by filtration
  10. customthe solvent by evaporation

Sources & evidence

ORD record
ord-98299ba7ce4f47d2a56c2374980739bb
Source dataset
uspto-grants-1988_05
Patent number
US04743607

Reaction notes

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