Quinoline → HCID 86751058, compound

HRID 265246Notes

Reaction equation

HRID 265246 reaction equation
[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21]([P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])[P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(O)C.[Pd]>[CH:1](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21]([P:30](=[O:37])([O:31][CH2:32][CH3:33])[O:34][CH2:35][CH3:36])[P:22](=[O:29])([O:23][CH2:24][CH3:25])[O:26][CH2:27][CH3:28])=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 54279876HCID 54279876, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86751058HCID 86751058, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tetraethyl [2-[2-(1-tridecynyl)phenyl]ethenylidene]bisphosphonate (1.5 g, 2.7 mmol) prepared according to Example 9 was dissolved in ethanol (17 ml), and quinoline (0.043 ml) and 5% palladium on calcium carbonate poisoned with lead (13 mg) was added. A balloon filled with hydrogen was attached to the flask after purging with hydrogen. After stirring for 3 hours the hydrogen pressure was released, and the reaction mixture was filtered through Celite. The filtrate was stripped. 1H NMR showed that only small amount of starting material had been converted to product. The hydrogenation was repeated using twice the amount of catalyst and quinoline for 4.5 hours, then workup as before. 1H NMR showed that a considerable amount of starting material remained. Three additional hydrogenations totaling 47 hours were done before the conversion was greater than 90%. Chromatography on silica eluting with 5% ethanol in petroleum ether (90°-110° C. boiling range) gave the product, 0.459 g, 0.825 mmol, 30.5% yield; 1H NMR (CDCl3) ∂0.88 (t, J=6.7 Hz, 3H), 1.03 to 1.45 (several m, 30H), 2.09 (m, 2H), 3.96 (m, 4H), 4.20 (m, 4H), 5.79 (dt, J=11.5, 7.4 Hz, 1H), 6.37 (d, J=11.4 Hz, 1H), 7.28 (m, 3H), 7.78 (d, J=7.3 Hz, 1H), 8.31 (dd, J=47.8, 28.4 Hz, 1H); CI mass spectrum m/z 557 (M+H)+.

Workup

  1. additionwas added
  2. customafter purging with hydrogen
  3. filtrationthe reaction mixture was filtered through Celite
  4. customfor 4.5 hours
  5. waitThree additional hydrogenations totaling 47 hours
  6. customChromatography on silica eluting with 5% ethanol in petroleum ether (90°-110° C. boiling range) gave the product, 0.459 g, 0.825 mmol, 30.5% yield

Sources & evidence

ORD record
ord-c1c80ad1797240d3aa73ea678fa26181
Source dataset
uspto-grants-1997_07
Patent number
US05648349

Reaction notes

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