N-(2-phenylethylidene)hydroxylamine

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% so aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration. combined with toluene (200 ml) for extraction The separated organic layer was washed twice with water (200 ml)

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

Procedure: Using the procedure of Example I, phenyl acetaldehyde oxime in chloroform is reacted with chlorine gas introduced at -5° to 0° C. To the resulting solution of 1-chlorophenyl acetaldehyde oxime is added dropwise with stirring a solution of potassium t-butoxide in t-butanol. The reaction is allowed to go to completion and any residual potassium t-butoxide is neutralized with hydrogen chloride gas. The precipitated potassium chloride is removed by filtration, and the filtrate concentrated under reduced pressure to provide the desired 1-(t-butoxy)-2-phenyl acetaldehyde oxime. introduced at -5° to 0° C The precipitated potassium chloride is removed by filtration the filtrate concentrated under reduced pressure

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

Procedure: Using the procedure of Example I, phenyl acetaldehyde oxime in chloroform is reacted with chlorine gas introduced at -5° to 0° C. To the resulting solution of 1-chlorophenyl acetaldehyde oxime is added dropwise with stirring a solution of potassium t-butoxide in t-butanol. The reaction is allowed to go to completion and any residual potassium t-butoxide is neutralized with hydrogen chloride gas. The precipitated potassium chloride is removed by filtration, and the filtrate concentrated under reduced pressure to provide the desired 1-(t-butoxy)-2-phenyl acetaldehyde oxime. introduced at -5° to 0° C The precipitated potassium chloride is removed by filtration the filtrate concentrated under reduced pressure

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration. combined with toluene (200 ml) for extraction The separated organic layer was washed twice with water (200 ml)

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

Procedure: A solution of N-chlorosuccinimide (3.25 g, 24 mmol) in abs. DMF (18 ml) was added to a solution of compound V (2.7 g, 20 mmol) in abs. DMF (12 ml) at a temperature of 30-40° C. within 20 min. Cooling in an ice bath was carried out if necessary. The reaction mixture was stirred for 3 h at RT and then mixed with diethyl ether (175 ml) and water (115 ml). The phases were separated and the aqueous phase was extracted with diethyl ether (2×75 ml). The combined organic extracts were washed successively with water (100 ml) and sat. NaCl solution (100 ml). The organic phase was dried and concentrated. Compound W was obtained as a yellowish-green oil (3.33 g) and immediately reacted further. Cooling in an ice bath The phases were separated the aqueous phase was extracted with diethyl ether (2×75 ml) The combined organic extracts were washed successively with water (100 ml) and sat. NaCl solution (100 ml) The organic phase was dried concentrated

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

Procedure: Phenylacetaldehyde (12.0 g, 7.8 ml, 0.1 mol) was dissolved in EtOH (360 ml) and mixed while stirring successively with hydroxylamine hydrochloride (10.4 g, 0.15 mol) and abs. pyridine (9.7 ml, 0.12 mol). After stirring for 1.5 h at RT, the reaction mixture was concentrated, the residue taken up in toluene (1×100 ml) and the solvent removed again under vacuum. The oily residue was stirred with EtOAc (350 ml) and water (90 ml) for 15 min. Subsequently, the phases were separated. The organic phase was washed with water (2×80 ml), dried and concentrated. The oil obtained crystallised after a short time. The oil was recrystallised from n-hexane (20 ml). Compound V was obtained as a white solid in a yield of 31% (4.13 g) having a melting point of 90-94° C. mixed the reaction mixture was concentrated the solvent removed again under vacuum The oily residue was stirred with EtOAc (350 ml) and water (90 ml) for 15 min Subsequently, the phases were separated The organic phase was washed with water (2×80 ml) dried concentrated The oil obtained crystallised after a short time The oil was recrystallised from n-hexane (20 ml)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration. combined with toluene (200 ml) for extraction The separated organic layer was washed twice with water (200 ml)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration. combined with toluene (200 ml) for extraction The separated organic layer was washed twice with water (200 ml)

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% so aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration. combined with toluene (200 ml) for extraction The separated organic layer was washed twice with water (200 ml)

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

Procedure: Using the procedure of Example I, phenyl acetaldehyde oxime in chloroform is reacted with chlorine gas introduced at -5° to 0° C. To the resulting solution of 1-chlorophenyl acetaldehyde oxime is added dropwise with stirring a solution of potassium t-butoxide in t-butanol. The reaction is allowed to go to completion and any residual potassium t-butoxide is neutralized with hydrogen chloride gas. The precipitated potassium chloride is removed by filtration, and the filtrate concentrated under reduced pressure to provide the desired 1-(t-butoxy)-2-phenyl acetaldehyde oxime. introduced at -5° to 0° C The precipitated potassium chloride is removed by filtration the filtrate concentrated under reduced pressure