3-oxo-3-phenylpropanenitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzoyl acetonitrile (2.0 g, 13.778 mmol) and methyl hydrazine (0.698, 15.156 mmol) in methanol (10 mL) was irradiated under microwave conditions at 110° C. for 90 min. The reaction mixture was cooled to rt and poured into rapidly stirred ice cold water. The obtained solid was collected by filtration, dried under vacuum and triturated with a mixture of pentane-hexane (˜10 mL) to yield a white solid (1.7 g, 71%). [1H-NMR (CDCl3, 300 MHz) δ 7.82-7.65 (m, 2H), 7.45-7.20 (m, 3H), 5.90 (s, 1H), 3.75 (s, 3H), 3.55 (s, 2H); LCMS RtA=0.824 min; [M+H]+=174.1] was irradiated under microwave conditions at 110° C. for 90 min poured into rapidly stirred ice cold water The obtained solid was collected by filtration dried under vacuum triturated with a mixture of pentane-hexane (˜10 mL)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1 g (7 mmol) of α-cyanoacetophenone, 8 g (43 mmol) of 1,2-dibromoethane, 0.1 g (0.4 mmol) of 18-crown-6 and 4 g (69 mmol) of potassium fluoride are heated under reflux for 18 h as a heterogeneous system in 10 ml of dichloromethane. After cooling, the mixture is filtered, the organic phase is washed with H2O and the solvent is evaporated in vacuo after drying over Na2SO4. The residue is chromatographed on a silica gel using CH2Cl2. 0.25 g (20% of theory) of 1-benzoyl-1-cyanocyclopropane are obtained in this manner as a colorless oil, After cooling the mixture is filtered the organic phase is washed with H2O the solvent is evaporated in vacuo after drying over Na2SO4 The residue is chromatographed on a silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A heptane washed suspension of 7.6 g (0.189 mole) of 60% NaH/mineral oil in 400 ml of anhydrous toluene was treated portion-wise with 25.0 g (0.172 mole) of benzoylacetonitrile under a nitrogen atmosphere. After stirring for 1 hour, 33.0 g (0.189 mole) of ethyl bromoacetate (97%) was added in one portion. The reaction was heated at reflux for 4 hours, then allowed to cool to room temperature and stirred for 20 hours. Water (500 ml) was added, and the toluene layer was extracted with water (500 ml). The toluene layer was dried over MgSO4, filtered, and the solvent evaporated under reduced pressure (42.9 g). The residual oil was fractionally distilled under vacuum to give 21.4 g (54%) of pure product. A heptane washed The reaction was heated at reflux for 4 hours stirred for 20 hours the toluene layer was extracted with water (500 ml) The toluene layer was dried over MgSO4 filtered the solvent evaporated under reduced pressure (42.9 g) The residual oil was fractionally distilled under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzoylacetonitrile (510 mg, 3.51 mmol) and conc. NH4OH (4 mL, 56.0 mmol) in a sealed tube was stirred at 80 C for 20 h. After cooling, solids precipitated out, which were collected by filtration, dried on vacuum to give (Z)-3-amino-3-phenylacrylonitrile (95 mg). After cooling solids precipitated out which were collected by filtration dried on vacuum

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzoylacetonitrile (9.94 g, 0.0685 mole), malononitrile (11.3 g, 0.17 mole), ammonium acetate (5.4 g, 0.07 mole) and ethanol (100 mL) was heated at reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was diluted with water (50 mL) and concentrated hydrochloric acid (7.5 mL) was added dropwise over 5 minutes. The resulting precipitate was collected by filtration and washed with water and ligroin. The yield was 10.0 g (76%), m.p. 92°-98° C. was heated at reflux for 1.5 hours was added dropwise over 5 minutes The resulting precipitate was collected by filtration washed with water and ligroin