HCID 57971179, compound → 6-(3,3-Diethoxypropyl)quinoline

HRID 1966367Notes

Reaction equation

HRID 1966367 reaction equation
[CH2:1]([O:3][CH:4]([O:17][CH2:18][CH3:19])[C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[CH3:2]>[Pd].C1COCC1>[CH2:18]([O:17][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[CH3:19]

Participants

4

Reactant 1

HCID 57971179HCID 57971179, compound

Product 1

HCID 579711766-(3,3-Diethoxypropyl)quinolineYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(3,3-diethoxyprop-1-yn-1-yl)quinoline (22, 56 mg, 0.22 mmol) and 10% palladium on carbon (5 mg) in THF (5 mL) was hydrogenated under H2 at 1 atm for 6 h. The reaction mixture was filtered through a celite bed and the celite bed was washed with THF (2×2 mL). The combined filtrates were concentrated under the reduced pressure to afford 6-(3,3-diethoxypropyl)quinoline (23, 56 mg, 57 mg theoretical, 98% yield) as a clear oil, which was found to be sufficiently pure to be used in the subsequent reaction without further purification and was identical to the material made from Method A in every comparable aspect.

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed
  2. washthe celite bed was washed with THF (2×2 mL)
  3. concentrationThe combined filtrates were concentrated under the reduced pressure

Sources & evidence

ORD record
ord-9fbbc84113dc4b25a4ca4a312b023d1f
Source dataset
uspto-grants-2013_04
Patent number
US08420645B2

Reaction notes

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