Ethanol → HCID 136342841, compound

HRID 1381502Notes

Reaction equation

HRID 1381502 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH2:7][C:6](=O)[C:5]=2[CH:4]=[CH:3][N:2]=1.[NH2:12][OH:13].C(O)C>N1C=CC=CC=1>[OH:13][N:12]=[C:6]1[CH2:7][CH:8]=[CH:9][C:10]2[CH:1]=[N:2][CH:3]=[CH:4][C:5]1=2

Participants

5

Reactant 3

HCID 702EthanolHCID 787HydroxylamineHCID 14276097HCID 14276097, compound

Product 1

HCID 136342841HCID 136342841, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isoquinolin-5-one (21.57g, 0.147M) and hydroxylamine (15.55g, 0.22M) together with approximately 300 ml of dry ethanol and 75 ml of pyridine were 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-73ee56fba44b43a3b7404bc04eed1a23
Source dataset
uspto-grants-1989_02
Patent number
US04803210

Reaction notes

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