2-Amino-3-chloropyridine

Light green solid

A sample of 3-chloro-2-nitropyridine (1.00 g, 6.31 mmol) was dissolved in methanol (10 mL), treated with Tin(II) chloride (5.98 g, 31.54 mmol) followed by concentrated HCl (2.63 mL, 31.54 mmol). The reaction mixture was allowed to stir overnight at rt. The solution was then diluted with ethyl acetate and washed with IN NaOH solution. The organic phase was then washed with concentrated NaHCOTo a stirred solution of 3-chloro-2-nitropyridine (1.00 g, 6.31 mmol) in EtOH (13 ml) were added a 2 M HCl aqueous solution (1.30 ml, 2.60 mmol) and iron (2.37 g, 42.4 mmol) at 0° C. The resulting mixture was stirred for 2.5 h at room temperature. Celite (2.40 g) was added. The mixture was filtered over a celite pad and evaporated to give a dark oil that was purified by elution through a SCX cartridge. The title compound D54 (0.34 g, 2.59 mmol, 41percent yield) was obtained as a dark solid. UPLC: rt=0.27 min, peaks observed: 129 (M+1, 100percent) and 131 (M+1, 33percent). C2, 3-Dichloropyridine (5.0 g, 34 mmol) and ammonium hydroxide (125 ml) were placed in a steel bomb and heated at 190 In a 250 ml three-necked flask, 0.053 mol (5.00 g) of 2-aminopyridine was added, Placed in 10 water bath.Constantly stirring, Add 0.11 mol of 13percent (mass concentration, The same) NaClO solution, Slowly dropping 0.3 mol of 36percent (mass concentration, The same below) hydrochloric acid.Constant temperature 10 reaction 2h, The temperature was raised to 25 ° C and the reaction was continued for 4 h.At last, The reaction was terminated by cooling the ice water to 10 ° C.The reaction solution was adjusted to pH> 8 with 5 mol / L NaOH solution, Filtration separation, Deionized water, And the filtrate and the washing liquid were extracted with dichloroethane solvent, Recovery of 2-aminopyridine and its chloride.The resulting solid precipitate and the dichloroethane extract were combined, Dissolved in 10percent dilute hydrochloric acid, filter.The filtrate was adjusted to pH = 4 with 5 mol / L NaOH solution, Extracted with dichloroethane solvent, The reaction product was separated to give 5.82 g of the reaction product.GC-MS analysis (Figure 1) shows that, The product contained 2-amino-5-chloropyridine 84.2percent2-amino-3-chloropyridine 12.1percent2-amino-3, 5-dichloropyridine 0.5percent2-aminopyridine 3.2percent. Calculated, 2-aminopyridine molar conversion of 95percentThe yield of 2-amino-5-chloro-pyridine was 71.6percent.Following the procedure of and substituting equal molar amounts of the following for 3-amino-2-chloropyridine: 4-amino-3-chloropyridine, 3-amino-4-chloropyridine, and

Molecular Weight:128.56
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.0141259
Monoisotopic Mass:128.0141259
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes