2,4-DINITRO-2'-METHOXYDIPHENYLAMINE synthesis
- Product Name:2,4-DINITRO-2'-METHOXYDIPHENYLAMINE
- CAS Number:14038-08-5
- Molecular formula:C13H11N3O5
- Molecular Weight:289.24
Yield:14038-08-5 97%
Reaction Conditions:
with potassium carbonate in tetrahydrofuran; for 18.75 h;Inert atmosphere;
Steps:
15.a
To a solution of 2,4- dinitrofluorobenzene (I) (1.86 g, 10 mmol) and 2-methoxyaniline (1.24 mL, 11 mmol) in anhydrous tetrahydrofuran (25 mL) is added K2CO3 (2.9 g, 21 mmol). The reaction mixture is stirred under argon for 18.75 h and filtered (CHCl3 rinse, 4 x). The filtrate is concentrated at reduced pressure, and the residue is crystallized (ethanol) to give 2.81 g (97%) of 2 as an orange solid, mp 165°-166 °C [lit: 165 °C](van Opstall, 1933). IR 3338, 2926, 1522, 1223 cm"1; 1HNMR (CDCl3) δ 3.86 (s, 3H, OCH3), 7.02-7.07 (m, 2H, 4',6'-ArH), 7.09 (d, J= 9.1 Hz, IH, 6-ArH), 7.30-7.35 (m, 2H, 3',5'-ArH), 8.15 (dd, J= 9.1 Hz, 2.4 Hz, IH, 5-ArH), 9.17 (d, J= 2.4 Hz, IH, 3-ArH), 9.86 ppm (bs, IH5 NH).
References:
WO2010/33643,2010,A2 Location in patent:Page/Page column 59; 60
