O-Allylhydroxylamine hydrochloride

After 500 mg of hydroxyphthalimide (Aldrich) was dissolved in 5 ml of dimethylformamide under argon flow, 0.3 ml of allyl iodide (Aldrich) was added, and 0.5 ml of 1, 8-diazabicyclo[5.4.0]undec-7-ene (Aldrich) was slowly added. After the mixture was stirred at room temperature for 1 hour and 20 minutes, the reaction was stopped by adding a 2 N hydrochloric acid solution. The reaction liquid was diluted by adding 20 ml of ethyl acetate, followed by drying over magnesium sulfate and then filtering. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate/hexane (1:5) and then dried to obtain 498 mg of a compound (yield: 80percent). The compound was dissolved in 5 ml of dichloromethane, and 0.11 ml of methyl hydrazine (TCI) was slowly added at 0° C. After the reaction liquid was stirred at room temperature for 2 hours, the temperature was again lowered to 0° C. The generated solid was then filtered out, and 1 ml of a 4 M-hydrochloric acid dioxane solution (Aldrich) was added to the residual filtrate, followed by filtration and drying, to obtain 236 mg of a solid (yield: 88percent). 16 mg of the obtained solid and 66 mg of SAC-0906 obtained as obtained above were dissolved in 1 ml of pyridine (Aldrich) under argon flow, followed by stirring at 80° C. for 4 hours. After the temperature was lowered to room temperature, 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 filtering. 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-1011 (63 mg, yield: 86percent). Under nitrogen gas environment, the reactor was put into acetate 810kg (molecular weight 74, 11.0kmol), hydroxylamine hydrochloride 500kg (molecular weight 69.5, 7.2kmol), 2kgDMF, stirred for 0.5 hour, to maintain 20-30 , dropping concentration of 30 mass percent sodium hydroxide solution 1000kg (7.5kmol), after the completion of dropwise addition, the reaction was kept 1 hour;After completion of the reaction, the reaction mixture was added to 2kg benzyl triethyl ammonium chloride and 970 kg of 1, 3-dichloropropene (molecular weight 111, 8.7kmol), was added dropwise a concentration of 30 mass percent sodium hydroxide solution 1000kg (7.5kmol ), and the reaction temperature was controlled at 30-40 deg.] C, the reaction was stirred for 1 hour;To the reaction solution was added at a concentration of 30percent by mass of hydrochloric acid 1000kg (8.2kmol), the reaction was warmed to 50-60 , incubated for 3 hours, the reaction was cooled to room temperature, added to a concentration of 30 mass percent sodium hydroxide solution and to pH7 -, toluene was added to 500kg, and extracted three times, to the water layer, the toluene solution of hydroxylamine O- allyl chloride to give the product desolventizing 720kg hydroxylamine O- allyl chloride (molecular weight 107.5, 6.7kmol), yield 93.0percent, content ≥99percent.Ethyl O-allyl acetohydroxamate (154.85 g, 0.85mol, 1eq) was added into a solution of 3 mol/L hydrochloric acid (425mL, 1.275mol, 1.5eq) for reflux reaction, at same time magnetic stirring, and heated at 110 ° C and carry on reaction for 2h, the reaction solution was concentrated with a water pump and precipitated as a white solid, the white solid was pulverized with methanol and dried and obtained 783.8 g of white crystals, melting point is 170.3 ° C, the titration purity is 98.8percent, and the yield is 90percent

Used for cyclization of O-allyl oxime to form pyridine

Molecular Weight:109.55
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:109.0294416
Monoisotopic Mass:109.0294416
Topological Polar Surface Area:35.2
Heavy Atom Count:6
Complexity:28.1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes