2-cyano-N-propylacetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 500 mg (5.88 mmol) Cyanoacetic acid are dissolved in 30 ml dimethylformamide, 382 mg (6.47 mmol) n-propylamine, 874 mg (6.47 mmol) 1-hydroxy-1H-benzotriazole hydrate and 718 mg (5.88 mmol) 4-dimethylaminopyridine are added. The reaction mixture is stirred at 0° C., then 1.24 g (6.47 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred at room temperature for 18 hours, then water and ethyl acetate are added. The organic phase is dried over sodium sulfate and evaporated to dryness in vacuo. The residue is purified by preparative HPLC. The reaction mixture is stirred at room temperature for 18 hours The organic phase is dried over sodium sulfate evaporated to dryness in vacuo The residue is purified by preparative HPLC

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 500 mg (5.88 mmol) Cyanoacetic acid are dissolved in 30 ml dimethylformamide, 382 mg (6.47 mmol) n-propylamine, 874 mg (6.47 mmol) 1-hydroxy-1H-benzotriazole hydrate and 718 mg (5.88 mmol) 4-dimethylaminopyridine are added. The reaction mixture is stirred at 0° C., then 1.24 g (6.47 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred at room temperature for 18 hours, then water and ethyl acetate are added. The organic phase is dried over sodium sulfate and evaporated to dryness in vacuo. The residue is purified by preparative HPLC. The reaction mixture is stirred at room temperature for 18 hours The organic phase is dried over sodium sulfate evaporated to dryness in vacuo The residue is purified by preparative HPLC

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: To a solution of 2-aminobiphenyl (10.16 g) in HOAc (36 ml) was added water (18 ml) and concentrated hydrochloric acid (18 ml). The solution was cooled to -15° with stirring. To this mixture was added dropwise a solution of sodium nitrite (4.36 g) in water (18 ml), maintaining the internal temperature below -5°. The resulting clear purple solution was stirred an additional 10 min at -10°, and was then added to a solution of N-propyl-2-cyanoacetamide (Prepared according to Shulka, J. S., et al., Journal of the Indian Chemical Society, (1978) 55:281-283.) (9.08 g) in water (400 ml)/ethanol (200 ml) containing sodium acetate (80 g) which had been chilled to -4°. This mixture was stirred mechanically at 0° for 6 hours before being allowed to warm to room temperature over a 15 hr. period. The mixture was then diluted with water (600 ml) and stirred. After 51/2 hours, the precipitated solid was collected by filtration and was washed with water and hexane. There was thus obtained 19.47 grams (>100% crude yield) of title product as a 5:1 ratio of Z:E isomers, m.p. 180°-184°; 1H NMR (CHCl3 -d, characteristic peaks of Z-isomer only): 0.948 (t, 3H), 1.53 (m, 2H), 3.20 (q, 2H), 6.04 (br.t, exchangeable, 1H), 7.20-7.29 (m, 2H), 7.37-7.54 (m, 6H), 7.76 (d. 1H), 13.96 (br.s, exchangeable, 1H) ppm. The solution was cooled to -15° maintaining the internal temperature below -5° The resulting clear purple solution was stirred an additional 10 min at -10° Prepared had been chilled to -4° This mixture was stirred mechanically at 0° for 6 hours stirred After 51/2 hours, the precipitated solid was collected by filtration was washed with water and hexane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 500 mg (5.88 mmol) Cyanoacetic acid are dissolved in 30 ml dimethylformamide, 382 mg (6.47 mmol) n-propylamine, 874 mg (6.47 mmol) 1-hydroxy-1H-benzotriazole hydrate and 718 mg (5.88 mmol) 4-dimethylaminopyridine are added. The reaction mixture is stirred at 0° C., then 1.24 g (6.47 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred at room temperature for 18 hours, then water and ethyl acetate are added. The organic phase is dried over sodium sulfate and evaporated to dryness in vacuo. The residue is purified by preparative HPLC. The reaction mixture is stirred at room temperature for 18 hours The organic phase is dried over sodium sulfate evaporated to dryness in vacuo The residue is purified by preparative HPLC