HCID 67271496, compound → HCID 67271462, compound

HRID 1696519Notes

Reaction equation

HRID 1696519 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][C:8](=[O:14])[CH2:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][C:8](=[O:14])[CH2:7]2

Participants

4

Reactant 1

HCID 67271496HCID 67271496, compound

Product 1

HCID 67271462HCID 67271462, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 1,2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 53.6 mmol) in MeOH (150 mL) was added 10% Pd/C (1.14 g, 1.07 mmol) and the mixture was stirred overnight under H2 (1 atm). After filtration, the filtrate was concentrated and the residue was suspended in acetone, filtered and precipitated with conc. HCl (10 mL). The resulting precipitate was collected, washed with H2O and acetone and recrystallized from MeOH/H2O to yield 6-amino-1,2-dihydroisoquinolin-3(4H)-one as a grey solid (6.7 g, 63% yield). 1H NMR (400 MHz, CD3OD): δ 7.22 (d, J=2.0 Hz, 1H), 7.20 (dd, J=8.4, and 2.4 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 3.01 (t, J=7.6 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H); MS (ESI) m/z: 163.0 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. filtrationfiltered
  4. customprecipitated with conc. HCl (10 mL)
  5. customThe resulting precipitate was collected
  6. washwashed with H2O and acetone
  7. customrecrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-a221a911ec4646898fda61b147295eca
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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