3-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-acrylonitrile → 3-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-propionitrile

HRID 1173978Notes

Reaction equation

HRID 1173978 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([CH:23]=[CH:24][C:25]#[N:26])[CH:17]=[CH:16]2>C(O)C.C(Cl)(Cl)Cl.[OH-].[Pd+2].[OH-].[C]>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([CH2:23][CH2:24][C:25]#[N:26])[CH:17]=[CH:16]2

Participants

5

Reactant 1

HCID 669415083-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-acrylonitrile

Product 1

HCID 210844023-[6-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-quinolin-2-yl]-propionitrileYield 17.6%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

The compound (574.4 mg) obtained in Example 119-6 was dissolved in ethanol (20 ml) and chloroform (10 ml). Then, the solution was added with 20% palladium hydroxide-carbon (172.3 mg) and then stirred at room temperature for 16 hours under a hydrogen atmosphere. After the reaction, the solution was filtrated through Celite and the solvent was then distilled off under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (101.9 mg) as a yellow solid.

Workup

  1. customAfter the reaction
  2. filtrationthe solution was filtrated through Celite
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7c66fcd8d21b4572ac0d1ea545416a8b
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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