Acetic Acid → HCID 10358700, compound

HRID 1590044Notes

Reaction equation

HRID 1590044 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8](=[O:18])[NH:9][C:10](=O)[C:11]3[C:16]=2[C:15]=1[CH:14]=[CH:13][CH:12]=3)([O-])=O.[CH3:19][OH:20].[C:21](O)(=O)[CH3:22]>[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:8](=[O:18])[N:9]([C@H:10]3[CH:6]4[CH2:21][CH2:22][N:9]([CH2:8][CH2:7]4)[CH2:10]3)[C:19](=[O:20])[C:11]3[C:16]=2[C:15]=1[CH:14]=[CH:13][CH:12]=3

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 372023HCID 372023, compound

Product 1

HCID 10358700HCID 10358700, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of (S)-2-(1-azabicyclo[2.2.2.]oct-3-yl)-2,3-dihydro-6-nitro-1H-benz[de]isoquinoline-1,3-dione (3.2 g; 8.8 mmol), prepared as in Example 2, in acetic acid (80 mL) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst (1.2 g) for 3 hours. The catalyst was removed by filtration, the filtrate concentrated to a small volume, and the residue dissolved in water. This aqueous solution was added dropwise to dilute NH4OH and the solid that precipitated was collected on a Buechner funnel. Drying under vacuum gave (S)-6-amino-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione (2.57 g; 7.93 mmol), m.p. 305°-308° C., [α]D25 -44.2° (c=0.373, MeOH).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to a small volume
  3. dissolutionthe residue dissolved in water
  4. additionThis aqueous solution was added dropwise to dilute NH4OH
  5. customthe solid that precipitated
  6. customwas collected on a Buechner funnel
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-c84f2b26e7954a8a971658aefa95a944
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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