Hydroxylamine, O-[(4-nitrophenyl)methyl]-, hydrochloride (1:1)

LIGHT YELLOW POWDER

0-(4-Nitrobenzyl)hydroxylamine Hydrochloride (19); A magnetically stirred suspension of compound 18 (2.00 g, 6.71 mmol) in EtOH (10 mL) was treated with HCl (20 mL of a cone, aqueous solution) and the resulting mixture heated at reflux for 3 h. The reaction mixture was then cooled slightly, HAfter 686 mg of hydroxyphthalimide (Aldrich) was dissolved in 10 ml of dimethylformamide under argon flow, 1 g of 4-nitrobenzyl chloride (Aldrich) was added, and 0.7 ml of 1, 8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. The mixture was stirred at room temperature for 1 hour, and the reaction was stopped by adding a 2 N hydrochloric acid solution, followed by filtration with ethyl acetate. The solid was again dissolved in ethanol and then recrystallized, followed by filtration and drying, to obtain 1.19 g of a white solid (yield: 87percent). 500 mg of the obtained white solid was dissolved in 15 ml of acetonitrile, and 0.06 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. 3 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the solution, followed by filtration and drying, to obtain 139 mg of a solid (yield: 41percent). 23 mg of the obtained solid and 50 mg of SAC-0906 obtained as obtained above were dissolved in 2 ml of pyridine (Aldrich) under argon flow, followed by stirring at room temperature for 14 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-1111 (28 mg, yield: 44percent).

A strong UV chromophore used in derivatization of reducing sugars for ultraviolet absorption detection in HPLC analyses.

Molecular Weight:204.61
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:204.0301698
Monoisotopic Mass:204.0301698
Topological Polar Surface Area:81.1
Heavy Atom Count:13
Complexity:149
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes