Benzenamine, 2-nitro-6-(phenylmethoxy)- synthesis
- Product Name:Benzenamine, 2-nitro-6-(phenylmethoxy)-
- CAS Number:89521-54-0
- Molecular formula:C13H12N2O3
- Molecular Weight:244.25
Yield:89521-54-0 99%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at -10 - 25; for 18 h;Inert atmosphere;
Steps:
1 Step 1 - 2-Benzyloxy-6-nitro-aniline
To a solution of 2-amino-3-nitro-phenol (60.0 g, 389 mmol, CAS 2835-97-4) and K2CO3 (107 g, 778 mmol) in DMF (1000 mL) was added BnBr (79.9 g, 467 mmol) at -10 °C. The reaction was then warmed to 25 °C and stirred for 18 hours. On completion, the reaction mixture was quenched by addition H2O (1000 mL), and extracted with ethyl acetate (3 X 5000 mL). The combined organic layers were washed with brine (3 X 500 mL) and dried over Na2SO4, filtered and concentrated in vacuo to give a crude product. The residue was purified by silica gel column chromatography (PE: EA = 3: 1) to give the title compound (95.0 g, 99% yield) as brown solid.1H NMR (400MHz, CDCl3) d 7.77 (dd, J = 1.2, 8.8 Hz, 1H), 7.49 - 7.36 (m, 5H), 7.04 - 6.95 (m, 1H), 6.61 (dd, J = 7.6, 8.8 Hz, 1H), 6.48 (br s, 2H), 5.15 (s, 2H), LC-MS (ESI+) m/z 245.6 (M+H)+.
References:
WO2020/113233,2020,A1 Location in patent:Paragraph 00962; 003898-003900
