Ethanol → 8-Amino-5-nitroisoquinoline

HRID 12413

Reaction equation

HRID 12413 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2].Cl.[NH2:15]O.C(O)C.[OH-].[Na+]>CO>[NH2:15][C:11]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[C:10]=1[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 690855-NitroisoquinolineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 110846258-Amino-5-nitroisoquinolineYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-nitroisoquinoline (2.0 g) were added hydroxylamine hydrochloride (5.0 g) and ethanol (120 ml). A solution of sodium hydroxide (10 g) in methanol (65 ml) was slowly added at 50° C. over 90 min. The reaction mixture was poured into ice water (700 g) and the resulting precipitate was collected by filtration. The residue was washed with ethanol and dried under reduced pressure to give 8-amino-5-nitroisoquinoline (1.25 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washThe residue was washed with ethanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5e9a210e943d4c09b800007a646d13db
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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