ChemicalBook CAS DataBase List Butyl(2,4-dinitrophenyl)amine

Butyl(2,4-dinitrophenyl)amine synthesis

11synthesis methods

Product Name:Butyl(2,4-dinitrophenyl)amine
CAS Number:13059-86-4
Molecular formula:C10H13N3O4
Molecular Weight:239.23

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109-73-9 Synthesis

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13059-86-4
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Yield:13059-86-4 98.11%

Reaction Conditions:

with triethylamine in chloroform at 20; for 18 h;Inert atmosphere;

Steps:

To a mixture of 2-chloro-1,4-dinitrobenzene (3 g) and 1-butanamine (2.16 g) in 10 mL of dry chloroform was added triethylamine (4.49 g). The reaction was stirred under Ar at ambient temperature for 18 h. Solvent was removed in vacuo. The residue was treated with 10 mL water and extracted with ethyl acetate (2x20 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate solution (1x10 mL), distilled water (1x10 mL) and brine solution (1x10 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated in vacuo to obtain N-butyl-2,4-dinitroaniline(3.5 g, yield 98.11%): IR (neat) 3682, 3362, 3101, 2949, 2424, 1844, 1615, 1514, 1314, 1128, 920, 821, 735, 507 cm^-1; ¹H NMR (400 MHz, CDCl₃,)δ9.14 (d, J = 2.73 Hz, 1H), 8.55 (s, 1H), 8.24-8.28 (m, 1H), 6.92 (d, J = 9.57 Hz, 1H), 3.38-3.45 (m, 2H), 1.72-1.82 (m, 2H), 1.45-1.55 (m. 2H), 1.01 (t, J = 7.3 Hz, 3H); ¹³C NMR (400 MHz, CDCl₃,)δ148.6, 130.6, 124.6, 114.2, 43.6, 30.9, 20.3, 13.9; HRMS m/z: found 239.09, calculated 239.09

References:

Sattenapally, Narsimha;Wang, Wei;Liu, Huimin;Gao, Yong [Tetrahedron Letters,2013,vol. 54,# 48,p. 6665 - 6668] Location in patent:supporting information