Hydroxylamine, O-phenyl-, hydrochloride (1:1)

Representative Procedure for the Hydrazinolysis of N-Aryloxyphthalimides to Corresponding O-Arylhydroxylamines (Method 1A): Synthesis of Compound 1; Hydrazine monohydrate (0.401 mL, 8.2 mmol) was added slowly to a solution of N-phenoxyphthalimide 9 (652 mg, 2.73 mmol) in 10percent MeOH in CHClAfter 163 mg of hydroxyphthalimide (Aldrich), 99 mg of copper chloride (Aldrich), 230 mg of molecular sieve 4 (Aldrich), and 244 mg of phenyl boronic acid (Aldrich) were sequentially dissolved in 5 ml of dichloroethane (Aldrich) under argon flow, 0.09 ml of pyridine (Aldrich) was added, followed by stirring for 5 hours. The reaction liquid was exposed to air, followed by stirring for 14 hours, and then the molecular sieve was filtered out, followed by dilution with ethyl acetate. The solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:2) to obtain a compound (161 mg, yield: 67percent). The compound was dissolved in 3 ml of dichloromethane, and 0.10 ml of hydrazine hydrate (Aldrich) was slowly added at 0° C. The reaction liquid was stirred at room temperature for 2 hours, and the temperature was again lowered to 0° C. The generated solid was filtered out, and the residual filtrate was concentrated under reduced pressure, followed by addition of an aqueous sodium carbonate solution and then extraction with 20 ml of diethyl ether. 0.3 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the solution, followed by filtration and drying, to obtain 103 mg of a solid (yield: 99percent). 21 mg of the obtained solid and 50 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 70° C. for 1 hours. The reaction liquid was acidified by adding a 2 N hydrochloric acid solution, followed by extraction with 20 ml of diethyl ether, drying over magnesium sulfate, and filtration. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixed eluent of ethyl acetate/hexane (1:5) to obtain the target compound SAC-1115 (18 mg, yield: 31percent). Ethyl O-phenylacetohydroxamate (185.47 g, 0.85 mol, leq) was added to a solution of 3 mol/L hydrochloric acid (587 mL, 1.76 mol, 2.0 Oeq) for reflux reaction while magnetically stirring and heating to 110°. C reaction was carried out for 2.5 hours, and the reaction liquid was concentrated with water white powder and white solid. The white solid was pulverized with methanol and dried to obtain 118.7 g of white crystals. The melting point was 121.8 ° C, the titration purity was 99.5percent, and the yield was 81.5percent

Molecular Weight:145.59
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:145.0294416
Monoisotopic Mass:145.0294416
Topological Polar Surface Area:35.2
Heavy Atom Count:9
Complexity:59.5
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes