Ethyl Acetate → 5-Aminoisoquinoline

HRID 1054019Notes

Reaction equation

HRID 1054019 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-])=O.[NH4+].[Cl-].C(OCC)(=O)C>CCO.O.[Fe]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 690855-Nitroisoquinoline

Product 1

HCID 707665-AminoisoquinolineYield 54%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-nitro-isoquinoline (150 g, 0.861 mol) in EtOH/H2O=4:1 (5 L) was added NH4Cl (92.2 g, 1.723 mol) and Fe (193 g, 3.445 mol) at room temperature. Then the mixture was heated to 80° C. and stirred for 10 hours. TLC (petroleum ether:ethyl acetate=1:1) showed complete conversion. The mixture was cooled to room temperature and filtered through a pad of celite. The filter cake was washed with EtOH (2 L×2) and the filtrate concentrated under vacuum. The residue was extracted with EtOAc (500 mL×10) and the combined layers dried over Na2SO4, filtered and then concentrated under vacuum to afford 5-amino-isoquinoline (67 g, 54%) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washThe filter cake was washed with EtOH (2 L×2)
  4. concentrationthe filtrate concentrated under vacuum
  5. extractionThe residue was extracted with EtOAc (500 mL×10)
  6. dry with materialthe combined layers dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f97150261dd4ee5a42172760d53e468
Source dataset
uspto-grants-2016_07
Patent number
US09394286B2

Reaction notes

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