ChemicalBook CAS DataBase List 2-CHLORO-4-N-NITRO(AMINOPYRIDINE)

2-CHLORO-4-N-NITRO(AMINOPYRIDINE) synthesis

3synthesis methods

Product Name:2-CHLORO-4-N-NITRO(AMINOPYRIDINE)
CAS Number:14432-13-4
Molecular formula:C5H4ClN3O2
Molecular Weight:173.56

19798-80-2 Synthesis

19798-80-2
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14432-13-4
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Yield:14432-13-4 85%

Reaction Conditions:

with sulfuric acid;nitric acid at 0 - 20; for 13 h;

Steps:

4-Amino-2-chloropyridine (10.0 g, mol) was carefully added to 70 mL of concentrated sulfuric acid at 0 °C with ice bath. To the suspension was added 70 mL of 70 % nitric acid dropwise while the inside temperature was maintained below 10 ⁰C with salt-ice bath. The reaction mixture was stirred for Ih at room temperature and then poured onto 300.0 g of crushed ice and allowed to cool to 10 °C for 12h. The cream-colored precipitate was filtered and washed well with ice water. The aqueous layer was treated with pallet NaOH until the pH of the solution reached at 3. The white solid was separated from the aqueous solution and filtered. The collected solid was dried to give 13.0 g of 2-Chloro-4-nitroaminopyridine in 85% yield, mp 163-164 ⁰C; UV (H₂O) λ_max 299.0 (ε 11880, pH 11), ¹H-NMR (DMSO₅ 500 MHz) δ 8.42 (d, J= 5.5, IH), 7.53 (d, J = 2.0, IH), 7.40 (dd, J= 5.5, 2.0, IH), 2.52 (s, IH); ¹³C-NMR (DMSO₅ 125 MHz) δ 151.51, 151.29, 145.89, 112.49, 112.26.

References:

WO2007/47793,2007,A2 Location in patent:Page/Page column 86

14432-12-3 Synthesis