HCID 131724372, compound → HCID 20636416, compound

HRID 2252834Notes

Reaction equation

HRID 2252834 reaction equation
N1C=CC=C(C=C[N:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])C=1>CO.C1COCC1.[Pd]>[N:9]1[CH:18]=[CH:17][CH:16]=[C:11]([CH2:12][CH2:13][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:19])[NH:9][CH:18]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 131724372HCID 131724372, compound

Product 1

HCID 20636416HCID 20636416, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

80 g (322 mmol) of an (E/Z) mixture of 4-[2-(pyridin-3-yl)-vinyl-2H-isoquinolin-1-one in 3100 ml of methanol/THF 1:1 are hydrogenated in the presence of 15.2 g of Pd/C (10%). Filtration and concentration by evaporation yield the crude product. Recrystallisation by dissolving in 650 ml of boiling ethanol, hot filtration, cooling and addition of 1 l of diethylether and 0.2 l of hexane yield colourless 4-[2-(pyridin-3-yl)-ethyl]-2H-isochinolin-1-one; m.p. 187-188° C.

Workup

  1. filtrationFiltration and concentration
  2. customby evaporation
  3. customyield the crude product
  4. customRecrystallisation
  5. dissolutionby dissolving in 650 ml of boiling ethanol
  6. filtrationhot filtration
  7. temperaturecooling
  8. additionaddition of 1 l of diethylether and 0.2 l of hexane

Sources & evidence

ORD record
ord-23c682bef3084893a111b6d1246c8298
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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