3-[2-(Quinolin-2-yl)ethenyl]benzaldehyde → HCID 22617026, compound

HRID 843248Notes

Reaction equation

HRID 843248 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]>[C].[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]

Participants

3

Reactant 1

HCID 538887303-[2-(Quinolin-2-yl)ethenyl]benzaldehyde

Product 1

HCID 22617026HCID 22617026, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundSolvent

Procedure

5.5 g (21.2 mmol) of 3-[2-(2-quinolyl)ethenyl]benzaldehyde was dissolved in 500 ml and hydrogenated in the presence of 1.1 g of 10% palladium carbon at atmospheric pressure at room temperature for 10 hours under stirring. The 10% palladium carbon was filtered out through celite, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give 2.8 g (10.7 mmol) of the title compound in a yield of 51%.

Workup

  1. filtrationThe 10% palladium carbon was filtered out through celite
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-c41498e21aa043a09a5b0a727a77ca1e
Source dataset
uspto-grants-2002_04
Patent number
US06376671B1

Reaction notes

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