O-[(3-fluorophenyl)methyl]hydroxylamine;hydrochloride

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

実験手順: A solution of 3-fluoro-4-methoxyacetophenone (0.063 g, 0.377 mmol), O-(3-fluorobenzyl)hydroxylamine hydrochloride (0.100 g, 0.569 mmol) and pyridine (0.14 ml, 1.73 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with water. The suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a white solid. The crude product was purified by column chromatography (SiO2), eluting with 95:5 petrol/ethyl acetate, to give 3′-fluoro-4′-methoxyacetophenone-O-3-fluorobenzyloxime (CP9-126) as a white solid (0.099 g, 90%), m.p. 67°. at reflux under nitrogen for 4 h The solution was concentrated to a pale yellow oil which was diluted with water The suspension was extracted with dichloromethane (×3) The combined organic phases were washed with water and brine dried over magnesium sulphate filtered concentrated to a white solid The crude product was purified by column chromatography (SiO2) eluting with 95:5 petrol/ethyl acetate

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

実験手順: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-fluorobenzyl)hydroxylamine hydrochloride (26) (59 mg, 0.332 mmol) according to the general procedure II-B defined above. After being heated at reflux for 48 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30262 (71 mg, 82%) as a pale-pink oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane. After being heated at reflux for 48 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

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

実験手順: A solution of 3-fluoro-4-methoxyacetophenone (0.063 g, 0.377 mmol), O-(3-fluorobenzyl)hydroxylamine hydrochloride (0.100 g, 0.569 mmol) and pyridine (0.14 ml, 1.73 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with water. The suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a white solid. The crude product was purified by column chromatography (SiO2), eluting with 95:5 petrol/ethyl acetate, to give 3′-fluoro-4′-methoxyacetophenone-O-3-fluorobenzyloxime (CP9-126) as a white solid (0.099 g, 90%), m.p. 67°. at reflux under nitrogen for 4 h The solution was concentrated to a pale yellow oil which was diluted with water The suspension was extracted with dichloromethane (×3) The combined organic phases were washed with water and brine dried over magnesium sulphate filtered concentrated to a white solid The crude product was purified by column chromatography (SiO2) eluting with 95:5 petrol/ethyl acetate

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

実験手順: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-fluorobenzyl)hydroxylamine hydrochloride (26) (59 mg, 0.332 mmol) according to the general procedure II-B defined above. After being heated at reflux for 48 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30262 (71 mg, 82%) as a pale-pink oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane. After being heated at reflux for 48 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

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

実験手順: A solution of 3-fluoro-4-methoxyacetophenone (0.063 g, 0.377 mmol), O-(3-fluorobenzyl)hydroxylamine hydrochloride (0.100 g, 0.569 mmol) and pyridine (0.14 ml, 1.73 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with water. The suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a white solid. The crude product was purified by column chromatography (SiO2), eluting with 95:5 petrol/ethyl acetate, to give 3′-fluoro-4′-methoxyacetophenone-O-3-fluorobenzyloxime (CP9-126) as a white solid (0.099 g, 90%), m.p. 67°. at reflux under nitrogen for 4 h The solution was concentrated to a pale yellow oil which was diluted with water The suspension was extracted with dichloromethane (×3) The combined organic phases were washed with water and brine dried over magnesium sulphate filtered concentrated to a white solid The crude product was purified by column chromatography (SiO2) eluting with 95:5 petrol/ethyl acetate

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

実験手順: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-fluorobenzyl)hydroxylamine hydrochloride (26) (59 mg, 0.332 mmol) according to the general procedure II-B defined above. After being heated at reflux for 48 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30262 (71 mg, 82%) as a pale-pink oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane. After being heated at reflux for 48 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)