Methyl Acrylate → HCID 14773942, compound

HRID 2396496Notes

Reaction equation

HRID 2396496 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[N:13][OH:14])[NH2:12])=[CH:3]1.[H-].[Na+].[C:17](OC)(=O)[CH:18]=[CH2:19]>C1COCC1>[CH:18]([C:19]1[O:14][N:13]=[C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[N:12]=1)=[CH2:17]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 53404815HCID 53404815, compound

Product 1

HCID 14773942HCID 14773942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-1H-indole-3 carboxamide oxime (C. J. Swain et al, J Med Chem, 1991, 34, 147) (0.500 g, 2.64 mmol) was dissolved in dry THF (20 ml) with stirring, and treated with ground 4A molecular sieves (1.5 g) under nitrogen. After 30 minutes sodium hydride (80% dispersion in mineral oil) (0.087 g, 2.91 mmol) was added. The mixture was then heated to reflux. After 30 minutes the mixture was allowed to cool momentarily and a methyl acrylate (0.475 ml, 5.28 mmol) was added. The mixture was then heated to reflux for a further 3 hours. The reaction mixture was then allowed to cool and was filtered. The filter pad was then washed with THF (2×). The filtrate was then evaporated under reduced pressure. The residue was purified by silica-gel chromatography eluting with pentane EtOAc 3:1 to afford the title compound (D2) as a colourless oil that crystallised on standing rapt 53°-55° C.

Workup

  1. temperatureThe mixture was then heated to reflux
  2. temperatureto cool momentarily
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for a further 3 hours
  5. temperatureto cool
  6. filtrationwas filtered
  7. washThe filter pad was then washed with THF (2×)
  8. customThe filtrate was then evaporated under reduced pressure
  9. customThe residue was purified by silica-gel chromatography
  10. washeluting with pentane EtOAc 3:1

Sources & evidence

ORD record
ord-d90d18c4728449c892c5807abe5f2979
Source dataset
uspto-grants-1996_02
Patent number
US05492919

Reaction notes

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