ChemicalBook CAS DataBase List 4-fluoro-2-Methoxy-5-nitroaniline

4-fluoro-2-Methoxy-5-nitroaniline synthesis

8synthesis methods

Product Name:4-fluoro-2-Methoxy-5-nitroaniline
CAS Number:1075705-01-9
Molecular formula:C7H7FN2O3
Molecular Weight:186.14

4-FLUORO-2-METHOXYANILINE(551 mg, 3.90 mmol) is dissolved in dichloromethane (39.0 mL), concentrated sulfuric acid (1.85 mL) is added dropwise with stirring under ice-cooling, and then concentrated nitric acid (267 μL, 5.85 mmol) is added dropwise. After stirring for 3 hours under ice-cooling, saturated aqueous sodium bicarbonate was added until pH 8 was reached. After washing with saturated aqueous sodium bicarbonate solution, washing with saturated brine, the organic layer was dried over sodium sulfate and evaporated under reduced pressure to obtain 675 mg of the 4-fluoro-2-Methoxy-5-nitroaniline (yield 93%).

450-91-9 Synthesis

450-91-9
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1075705-01-9
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Yield:1075705-01-9 95%

Reaction Conditions:

with sulfuric acid;potassium nitrate at 0 - 5; for 2 h;Inert atmosphere;

Steps:

81 Preparation 81 : 4-fluoro-2-methoxy-5-nitroaniline

A solution of 4-fluoro-2-methoxyaniline (1590 mg, 11.27 mmol) in conc.H2S04 (9.55 ml_) was treated with solid KNO3 (1140 mg, 11.3 mmol) in portions while keeping the internal temperature below 5 °C. The resulting mixture was stirred for 2 h at 0 °C and mixture was poured into ice water (100 ml_), neutralized slowly with solid Na2CO3 and extracted with EtOAc (2 x 60 ml_). The organic layers were dried (Na2SO4), filtered and and concentrated to give the title compound (2 g, 95%).¹H NMR (400 MHz, CDCl3) d 7.42 (d, 1 H), 6.66 (d, 1 H), 3.96 (s, 3H), 1.60 (s, 2H); LC/MS m/z (M+H)⁺=186.8.

References:

WO2021/124155,2021,A1 Location in patent:Page/Page column 53; 93