Water → HCID 14929482, compound

HRID 2403219Notes

Reaction equation

HRID 2403219 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].CC(N(C)C)=O.[C:12]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:3][N:2]([CH3:1])/[CH:4]=[C:20](/[C:12](=[O:19])[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1)\[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 31374DimethylacetamideHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 14929482HCID 14929482, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Pyridinium p-toluene sulfonate (7.8 mg; 0.031 mmol) and DMF.DMA (5.35 mL; 40.3 mmol) were added to a solution of ethyl isonicotinoylacetate (6.0 g; 31.0 mmol) in anhydrous toluene (40 mL) and the mixture was heated to 90° C. for 3 hours. The mixture was cooled, water (50 mL) was added and the product was extracted with DCM (3×50 mL). The combined organic fractions were passed through a hydrophobic frit and the solvent was removed in vacuo to give the title compound as a purple oil (7.68 g; 99.8%). The compound was used directly without any further purification.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe product was extracted with DCM (3×50 mL)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d049829f72434d36829cf6cba526feb1
Source dataset
uspto-grants-2014_08
Patent number
US08802663B2

Reaction notes

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