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

17809-36-8

General procedure for the synthesis of 2-fluoro-6-nitroaniline from N-(2-fluoro-6-nitrophenyl)acetamide: 3 g (0.0151 mol) of N-(2-fluoro-6-nitrophenyl)acetamide (3a) was dissolved in 30 mL of concentrated H2SO4 and the reaction was stirred for 2 hr at 50 °C. After completion of the reaction, it was cooled to room temperature and the reaction solution was slowly poured into an ice bath and a large amount of precipitate was observed to be generated. The precipitate was collected by filtration and the acidic aqueous solution was extracted with ether. Purification by fast column chromatography afforded the target compound 2-fluoro-6-nitroaniline in 74% yield. The melting point of the product was 47-48 °C. 1H NMR (DMSO-d6) data: δ 7.82 (d, 1H, J=8.8 Hz, H-5), 7.42 (m, 1H, H-3), 7.25 (s, 2H, NH2), 6.63 (m, 1H, H-4). GC/MS analysis showed the molecular ion peak as 157 (M+H). Elemental analysis (C6H5FN2O2) Calculated values: C, 46.16; H, 3.23; F, 12.17; N, 17.94. Measured values: C, 46.18; H, 3.27; F, 12.15; N, 17.98.

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