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ChemicalBook CAS DataBase List N-cyclohexyl-3-nitropyridin-2-amine

N-cyclohexyl-3-nitropyridin-2-amine synthesis

3synthesis methods
-

Yield:61963-88-0 30%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 120;

Steps:

4.1.1. General synthesis of 1-2

General procedure: The mixture of 2-chloro-3-nitropyridine (3 mmol), correspondinganilines (3 mmol) and K2CO3 (3 mmol) were heated inDMF at 120 °C, for 3-4 h. The reaction mixture was allowed to coolto room temperature then diethyl ether was added. The organiclayer was washed with water dried over MgSO4, filtered and evaporated. The residue was crystallised from ethylacetate/nhexane. 4.1.1.1. N2-cyclohexyl-3-nitro-2-amino pyridine (1). Prepared from2-chloro-3-nitropyridine (0.47 g), cyclohexylamine (0.34 g) andK2CO3 (0.41 g) as described in general method. Yield. 0.19 g, (30%),yellow oily liquid. 1H-NMR δ ppm (CDCl3): 1.22-1.49 (m,5H),1.59-1.74 (m,1H), 1.75-1.79 (m,2H), 2.01-2.05 (m,2H), 4.21 (m,1H),6.56 (m,1H), 8.20 (br.s,1H), 8.36-8.38 (m,2H). 13C-NMR δ ppm(CDCl3): 24.7, 25.6, 32.9, 49.4, 111.2, 127.6, 135.3, 152.0, 155.9. MS(ESI) m/z: 222(M + H, 100%), C11H15N3O2.

References:

Karaaslan, Cigdem;Doganc, Fatima;Alp, Mehmet;Koc, Asli;Karabay, Arzu Zeynep;G?ker, Hakan [Journal of Molecular Structure,2020,vol. 1205,art. no. 127673]