Water → HCID 57720099, compound

HRID 1985631Notes

Reaction equation

HRID 1985631 reaction equation
[CH3:1][N:2]([CH3:18])[N:3]1[C:12]2[C:7](=[CH:8][C:9](I)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1.[CH2:19]([OH:22])[C:20]#[CH:21].O.C(OC(C)C)(C)C>CC#N.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]([CH3:18])[N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:21]#[C:20][CH2:19][OH:22])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1

Participants

8

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 7914Diisopropyl EtherHCID 57720066HCID 57720066, compound

Product 1

HCID 57720099HCID 57720099, compoundYield 181.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-dimethylamino-6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (2.77 g, 7.73 mol) in MeCN (70 ml), CuI (0.15 g, 0.773 mol) and TEA (37.5 ml, 270 mol) were added and stirred for 20 minutes and then warmed up to 50° C. To the reaction mixture propargyl alcohol (1.08 ml, 2.4 mmol) and Pd(PPh3)2Cl2 (0.27 g, 0.39 mol) were added and stirred at 50° C. for 3 hours. Then water (130 ml) and diisopropyl-ether (100 ml) were added, the pH was adjusted to 12, the layers were separated and H2O layer extracted with diisopropyl-ether (2×50 ml). To the water layer EtOH (14 ml) and charcoal were added, heated to the reflux temperature, and filtered through celite. Then the pH of H2O solution was adjusted to 6, extracted with DCM (200 ml), combined organic layers were evaporated to obtain the crude product. Precipitation from DCM-hexane afforded the title product (1.25 g, 56%).

Workup

  1. stirringstirred at 50° C. for 3 hours
  2. customthe layers were separated
  3. extractionH2O layer extracted with diisopropyl-ether (2×50 ml)
  4. additionTo the water layer EtOH (14 ml) and charcoal were added
  5. temperatureheated to the reflux temperature
  6. filtrationfiltered through celite
  7. extractionextracted with DCM (200 ml)
  8. customwere evaporated
  9. customto obtain the crude product
  10. customPrecipitation from DCM-hexane

Sources & evidence

ORD record
ord-b45590778fb14633a2d69c1b391d20f0
Source dataset
uspto-grants-2009_06
Patent number
US07547679B2

Reaction notes

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