Cesium carbonate → HCID 68028001, compound

HRID 1620082Notes

Reaction equation

HRID 1620082 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Cl[C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][N:57]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[N+:62]([C:59]1[CH:60]=[CH:61][C:56]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[N:57][CH:58]=1)([O-:64])=[O:63]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 783082-Chloro-5-nitropyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 68028001HCID 68028001, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Pyrrolidin-2-one (129 mg), cesium carbonate (412 mg), Pd2(dba)3 (116 mg), and Xantphos (146 mg) were added to a 1,4-dioxane (10 ml) solution containing 2-chloro-5-nitropyridine (200 mg) in a nitrogen atmosphere, followed by stirring at 100° C. for 5 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a light red solid of 1-(5-nitropyridin-2-yl)pyrrolidin-2-one (261 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-8884dcca97204f9b839c7aef33bf9669
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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