ChemicalBook CAS DataBase List 2-FLUORO-6-NITRO-PHENYLAMINE

2-FLUORO-6-NITRO-PHENYLAMINE synthesis

7synthesis methods

Product Name:2-FLUORO-6-NITRO-PHENYLAMINE
CAS Number:17809-36-8
Molecular formula:C6H5FN2O2
Molecular Weight:156.11

342-52-9 Synthesis

342-52-9
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17809-36-8
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Yield:17809-36-8 74%

Reaction Conditions:

with sulfuric acid at 50; for 2 h;

Steps:

5.1.2 2-Fluoro-6-nitroaniline (4)
3g (0.0151mol) of 52 N-(2-fluoro-6-nitrophenyl)acetamide (3a) are dissolved in 30ml of 53 concentrated H₂SO₄ and brought to 50°C for 2h. After cooling, the solution is poured into an ice bath and an abundant precipitate is observed. After filtration, the acidic aqueus solution is extracted with diethyl ether. The pure 9 compound is obtained through flash chromatography. Yield 74%. M.P. 47-48°C. ¹H NMR (DMSO-d₆): δ 7.82 (d, 1H, J=8.8MHz, H-5), 7.42 (m, 1H, H-3), 7.25 (s, 2H, NH₂), 6.63 (m, 1H, H-4). GC/MS: 157 (M+H). Anal. Calcd for (C₆H₅FN₂O₂): C, 46.16; H, 3.23; F, 12.17; N, 17.94. Found: C, 46.18; H, 3.27; F, 12.15; N, 17.98.

References:

Carta, Antonio;Bua, Alessandra;Corona, Paola;Piras, Sandra;Briguglio, Irene;Molicotti, Paola;Zanetti, Stefania;Laurini, Erik;Aulic, Suzana;Fermeglia, Maurizio;Pricl, Sabrina [European Journal of Medicinal Chemistry,2019,vol. 161,p. 399 - 415]

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399-31-5 Synthesis