Sodium hydride → 74839-90-0

HRID 2086786Notes

Reaction equation

HRID 2086786 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9]P(=O)(OCC)OCC)([O-:5])=[O:4].[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=O)=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[C:8](/[CH:9]=[CH:31]/[C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]=[CH:22][CH:23]=2)[CH:18]=[CH:19][CH:20]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 780724-QuinolinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 13675396Diethyl 3-Nitrobenzylphosphonate

Product 1

HCID 83255074839-90-0Yield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% in oil, 0.75 g) in N,N-dimethylformamide (20 ml) was added a solution of diethyl 3-nitrobenzylphosphonate (4.40 g) in N,N-dimethylformamide (20 ml). The mixture was stirred at room temperature for 15 minutes, then a solution of 4-quinolinecarbaldehyde (2.81 g) in N,N-dimethylformamide (20 ml) was added thereto. After stirring at 50° C. for 30 minutes, the mixture was poured into aqueous sodium bicarbonate, and extracted with ethyl acetate twice. The combined organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (chloroform-methanol (50:1)) to give 4-[(E)-2-(3-nitrophenyl)vinyl]quinoline (1.57 g) as a solid.

Workup

  1. stirringAfter stirring at 50° C. for 30 minutes
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic solution was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-b0d6eb6414534cd98f4506a1a9b11723
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…