Hydrochloric Acid → 5-aminoisoquinolin-1(2H)-one

HRID 1645901Notes

Reaction equation

HRID 1645901 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][NH:8][C:9]2=[O:14])([O-])=O.Cl>CC(O)=O.C(O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][NH:8][C:9]2=[O:14]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 2313785-Nitro-1,2-dihydroisoquinolin-1-one

Product 1

HCID 20725-aminoisoquinolin-1(2H)-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 4.0 g (21 mmol) of 5-nitroisoquinolinone in 100 ml HOAc and 0.5 g 5% Pd-C was hydrogenated at room temperature for 18 hours (three atmospheres). The mixture was filtered and concentrated to give a solid. The solid was dissolved in ethanol (50 ml) and 10 ml of saturated ethanolic HCl was added. The solution was cooled and the resulting solid was collected. It was dissolved in water and the solution was neutralized with 100 ml concentrated NH4OH. The precipitate was collected, dissolved in 150 ml of hot methanol, treated with charcoal, filtered, and diluted with water. Upon cooling, 1.10 g (32%) of the desired product was collected; mp 258°-259°.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customto give a solid
  4. temperatureThe solution was cooled
  5. customthe resulting solid was collected
  6. dissolutionIt was dissolved in water
  7. customThe precipitate was collected
  8. dissolutiondissolved in 150 ml of hot methanol
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. additiondiluted with water
  12. temperatureUpon cooling
  13. custom1.10 g (32%) of the desired product was collected

Sources & evidence

ORD record
ord-7bb4ae3214894ff58550f88c5acb89ef
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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