N-benzhydrylidenehydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of benzophenone (10.0 g), hydroxylamine hydrochloride (10.0 g), pyridine (50 ml), and absolute ethanol (50 ml) was pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa). The effluent was cooled and the solvent removed by rotary evaporation, and the residue stirred with cold water (50 ml). The crued oxime was filtered off and recrystallised from ethanol to afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5 for a batchwise preparation by microwave heating. was pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa) The effluent was cooled the solvent removed by rotary evaporation The crued oxime was filtered off recrystallised from ethanol to afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5 for a batchwise preparation by microwave heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of benzophenone (10.0 g), hydroxylamine hydrochloride (10.0 g), pyridine (50 ml), and absolute ethanol (50 ml) was pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa). The effluent was cooled and the solvent removed by rotary evaporation, and the residue stirred with cold water (50 ml). The crued oxime was filtered off and recrystallised from ethanol to afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5 for a batchwise preparation by microwave heating. was pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa) The effluent was cooled the solvent removed by rotary evaporation The crued oxime was filtered off recrystallised from ethanol to afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5 for a batchwise preparation by microwave heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Benzophenone oxime (3.94 g, 20 mmol), 1-bromo-2-chloroethane (28.7 g, 200 mmol) and dried, powdered potassium carbonate (5.53 g, 80 mmol) in acetone (60 ml) were heated at reflux for 72 h. The reaction mixture was cooled and filtered and the filtrate was evaporated to an oily residue which was purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1) to provide diphenylmethanone O-(2-chloroethyl)oxime (3.82 g, 73%) as an oil, tlc rf 0.36 (SiO2, heptane/ethyl acetate 9/1). were heated at reflux for 72 h The reaction mixture was cooled filtered the filtrate was evaporated to an oily residue which was purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Benzophenone oxime (3.94 g, 20 mmol), 1-bromo-2-chloroethane (28.7 g, 200 mmol) and dried, powdered potassium carbonate (5.53 g, 80 mmol) in acetone (60 ml) were heated at reflux for 72 h. The reaction mixture was cooled and filtered and the filtrate was evaporated to an oily residue which was purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1) to provide diphenylmethanone O-(2-chloroethyl)oxime (3.82 g, 73%) as an oil, tlc rf 0.36 (SiO2, heptane/ethyl acetate 9/1). were heated at reflux for 72 h The reaction mixture was cooled filtered the filtrate was evaporated to an oily residue which was purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis of 4-aminooxybutyric acid and 5-aminooxyvaleric acid are described in Tetrahedron, 23, 4441 (1967). Benzophenone oxime in N-methylpyrrolidone is reacted first with sodium then with γ-butyrolactone to provide N-diphenylmethylidene-4-aminooxybutyric acid which is subsequently hydrolyzed to form 4-aminooxybutyric acid. 5-aminooxyvaleric acid hydrochloric acid salt is prepared similarly by substituting γ-butyrolactone with γ-valerolactone. Aminooxyacetic acid is available as the hemihydrochloride from a commercial source.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis of 4-aminooxybutyric acid and 5-aminooxyvaleric acid are described in Tetrahedron, 23, 4441 (1967). Benzophenone oxime in N-methylpyrrolidone is reacted first with sodium then with γ-butyrolactone to provide N-diphenylmethylidene-4-aminooxybutyric acid which is subsequently hydrolyzed to form 4-aminooxybutyric acid. 5-aminooxyvaleric acid hydrochloric acid salt is prepared similarly by substituting γ-butyrolactone with γ-valerolactone. Aminooxyacetic acid is available as the hemihydrochloride from a commercial source.