Nitrogen → HCID 58869204, compound

HRID 2100343Notes

Reaction equation

HRID 2100343 reaction equation
C[O-].[Na+].N#N.[C:6]([O:9][CH3:10])(=[O:8])[CH3:7].[CH:11]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)=O>O1CCCC1>[NH:17]1[C:18]2[C:14](=[C:13]([CH:11]=[CH:7][C:6]([O:9][CH3:10])=[O:8])[CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6584Methyl AcetateHCID 333703Indole-4-carboxaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 58869204HCID 58869204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

48 g of sodium methoxide are added to 300 ml of tetrahydrofuran with stirring at 5° C. under a protective gas (N2), the suspension is cooled to 0° C., 70 ml of methyl acetate are added dropwise at from 0 to 3° C., and the mixture is stirred at this temperature for a further 45 minutes. A solution of 43 g of 4-formylindole (3) in 300 ml of tetrahydrofuran is subsequently added with stirring, during which the temperature does not exceed 3° C. The mixture is subsequently stirred at room temperature for a further two hours. For work-up, the reaction mixture is evaporated, and the residue is dissolved in methyl acetate and extracted with water. The organic phase obtained is dried, the solvent is removed under reduced pressure, and the residue is purified by chromatography on silica gel, giving 35 g (59% of theory) of a pale-beige crystalline residue of methyl 3-(1H-indol-4-yl)acrylate (4).

Workup

  1. stirringwith stirring, during which the temperature
  2. customdoes not exceed 3° C
  3. stirringThe mixture is subsequently stirred at room temperature for a further two hours
  4. customFor work-up, the reaction mixture is evaporated
  5. dissolutionthe residue is dissolved in methyl acetate
  6. extractionextracted with water
  7. customThe organic phase obtained
  8. customis dried
  9. customthe solvent is removed under reduced pressure
  10. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cf3ba060a5d94b57af448c0db969366b
Source dataset
uspto-grants-2009_08
Patent number
US07572796B2

Reaction notes

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