HCID 10081720, compound → HCID 67378758, compound

HRID 717768Notes

Reaction equation

HRID 717768 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:3][CH:2]=1>C(O)C.[Pt]=O>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 10081720HCID 10081720, compound

Product 1

HCID 67378758HCID 67378758, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

3-(Pyridin-4-yl)quinoline (1 g, 0.00485 mol) was dissolved in ethanol (30 mL). To this was added platinum oxide (0.4 g) under nitrogen atmosphere, and the reaction mixture was hydrogenated at 50 psi for 10 h. After completion of reaction (monitored by TLC), the catalyst was removed by filtration, the filtrate concentrated under reduced pressure and the residue purified by column chromatography (30% EtOAc:hexane on silica 100-200 mesh, diameter of column—2.5 cm, height of silica—approx. 5 inch) to provide the desired compound (0.4 g, 40% yield).

Workup

  1. customAfter completion of reaction (monitored by TLC)
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customthe residue purified by column chromatography (30% EtOAc:hexane on silica 100-200 mesh, diameter of column—2.5 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-5d6c697ae52748cea839aa224667e4a8
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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