ChemicalBook CAS DataBase List 4-Chloro-2,3-dimethylpyridine 1-oxide

4-Chloro-2,3-dimethylpyridine 1-oxide synthesis

4synthesis methods

Product Name:4-Chloro-2,3-dimethylpyridine 1-oxide
CAS Number:59886-90-7
Molecular formula:C7H8ClNO
Molecular Weight:157.6

83.0 g (0.49 mol) of 4-nitro-2,3-dimethylpyridine N-oxide and 90 g (1.54 mol) of NaCl were admixed with 1350 ml of CH3CN, 180 ml of aq. HCl (36%) and 16.6 g of benzyltributylammonium chloride, and the resulting suspension was boiled under reflux with stirring for 12 h. The resulting reaction mixture was adjusted to PH=9 using 350 ml of 20% NaOH, wherefor the existing precipitate largely dissolved. The organic phase was separated off, water was added to the aqueous phase until the precipitate had completely dissolved, and it was subsequently extracted using dichloromethane. The organic phases were combined and the solvent was removed under reduced pressure. 76.6 g (98.5%) of 4-Chloro-2,3-dimethylpyridine 1-oxide were obtained.

37699-43-7 Synthesis

37699-43-7
387 suppliers
$10.00/1g

59886-90-7
255 suppliers
$25.00/250 mg

Yield:59886-90-7 100%

Reaction Conditions:

with acetyl chloride in ethanol at 65; for 5 h;

Steps:

26 The synthesis of X4-349-4
To a solution of X4-348-3 (10.0 g, 59.47 mmol) in ethanol (100.0 mL) was slowly added acetyl chloride (10.6 mL, 148.68 mmol). The mixture was stirred at 65 °C for 5 h. The solvent was removed under reduce pressure, diluted with water and DCM, aqueous NaOH (5 0%) was added dropwise to adjust pH to 7.5-8.5. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuum. The crude X4-349-4 (9.4 g, 100% yield) was used in next step without further purification. LCMS (Agilent LCMS 1200-6120, Column: Waters XBridge C18 (50 mm*4.6 mm*3.5 iim); Column Temperature: 40 °C; Flow Rate: 2.0 mL/min;Mobile Phase: from 90% [(total 10mM AcONH4) water/CH3CN = 900/100 (v/v)] and 10% [(total 10mM AcONH4) water/CH3CN = 100/900 (v/v)] to 10% [(total 10mM AcONH4) water/CH3CN = 900/100 (v/v)] and 90% [(total 10mM AcONH4) water/CH3CN = 100/900 (v/v)] in 1.6 mm, then under this condition for 2.4 mm, finally changed to 90% [(total the 10mM AcONH4) water/CH3CN = 900/100 (v/v)] and 10% [(total 10mM AcONH4) water/CH3CN = 100/900 (v/v)] in 0.1 mm and under this condition for 0.7 mm). Purity: 95.35%; Rt = 0.65 mm; MS Calcd.: 157.0; MS Found: 158.4[M+H]t

References:

X4 PHARMACEUTICALS, INC.;BOURQUE, Elyse Marie Josee;SKERLJ, Renato WO2017/223229, 2017, A1 Location in patent:Paragraph 00452; 00453

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22710-07-2 Synthesis