Methanol → HCID 14956184, compound

Temperature

55 °C

After 3.63 g (68.4 mmol) of acrylonitrile and 2.2 ml of 40% methanol solution of N-benzyltrimethyl-ammonium hydroxide was added to a solution of 10.0 g (57.1 mmol) of methyl 2-indolecarboxylate in 150 ml of 1,4-dioxane, the mixture was stirred at 55° C. for an hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was added to a mixture of 5 ml of acetic acid and 500 ml of water. The aqueous layer was extracted twice with methylene chloride and the combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 13.0 g of methyl 1-(2-cyano-ethyl)-2-indolecarboxylate.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe resulting residue was added to a mixture of 5 ml of acetic acid and 500 ml of water
3. extractionThe aqueous layer was extracted twice with methylene chloride
4. washthe combined extracts were washed with water
5. dry with materialAfter drying over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-9f3f855a90f64c1eb600d486baae4319

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06169107A