Dimethyl Sulfoxide → 6-Iodo-4-propyl-quinoline-3-carbonitrile

HRID 1297728Notes

Reaction equation

HRID 1297728 reaction equation
C(OC(=O)[C:5]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([I:23])[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:24]#[N:25])([CH2:11][CH3:12])C(OCC)=O)C.[Cl-].[Li+].O.CS(C)=O>CCCCCC.C(OCC)(=O)C>[I:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([C:24]#[N:25])=[C:13]2[CH2:5][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 433294Lithium ChlorideHCID 585858492-(3-Cyano-6-iodo-quinolin-4-yl)-2-ethyl-malonic acid diethyl ester

Product 1

HCID 585858666-Iodo-4-propyl-quinoline-3-carbonitrileYield 23%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-cyano-6-iodo-quinolin-4-yl)-2-ethyl-malonic acid diethyl ester (example 71a, 250 mg, 0.54 mmol), lithium chloride (45 mg, 0.72 mmol), water (10 uL, 0.54 mmol), and dimethylsulfoxide (10 uL) was heated at 180 degrees for 1 hour. After cooling to the room temperature, the reaction was quenched with water, followed by addition of ethyl acetate. The insoluble material was removed by filtration through a plug of celit with ethyl acetate. The water layer was extracted with ethyl acetate two more times. The organic layers were combined, washed with brain, dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product as dark viscous oil. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 10-20% ethyl acetate in hexane in 30 min) afforded 6-iodo-4-propyl-quinoline-3-carbonitrile (40 mg, 23%) as a solid. LC-MS m/e 323 (MH+).

Workup

  1. temperaturewas heated at 180 degrees for 1 hour
  2. customthe reaction was quenched with water
  3. additionfollowed by addition of ethyl acetate
  4. customThe insoluble material was removed by filtration through a plug of celit with ethyl acetate
  5. extractionThe water layer was extracted with ethyl acetate two more times
  6. washwashed with brain
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product as dark viscous oil

Sources & evidence

ORD record
ord-25619f7bbf904a4d82e6e8b53a0228dc
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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