N-(2-FLUOROPHENYL)ANTHRANILIC ACID synthesis
- Product Name:N-(2-FLUOROPHENYL)ANTHRANILIC ACID
- CAS Number:54-58-0
- Molecular formula:C13H10FNO2
- Molecular Weight:231.22
Yield:54-58-0 69.3%
Reaction Conditions:
with copper (I) iodide;potassium carbonate in lithium hydroxide monohydrate;N,N-dimethyl-formamide at 100; for 2 h;Microwave irradiation;
Steps:
2-((2-fluorophenyl)amino)benzoic acid (33)
was synthesized using general procedure C from 2-iodo benzoic acid (29) (496 mg, 2 mmol), 2-fluoro aniline (0.1 mL, 1 mmol), K2CO3 (416 mg, 3 mmol), CuI (200 mg, 1.04 mmol) and 5 mL DMF/H2O (9:1). The reaction was subjected to 300 Watt microwave irradiation with the internal temperature maintained at 100 oC for 2 h. After completion of the reaction was analyzed by TLC, 1 N HCl (~ 4 mL) was added to the reaction mixture to obtain a final solution pH of 6.0. The solvent was then removed under reduced pressure. The crude compound was isolated on SiO2 using 1:1 hexane/EA to give after recyrstalization from ethanol, 160 mg (69.3%) of grey-black crystals. MP = 182.6-182.9 1H NMR (500 MHz, MeOD4): δ 6.79-6.83 (m, 1 H, Ar), 7.08-7.22 (m, 4 H, Ar), 7.366-7.401 (m, 1 H, Ar), 7.47-7.50 (m, 1 H, Ar), 8.00-8.03 (m, 1 H, Ar). Anal. Calcd. for C13H10FNO2: C, 67.53; H, 4.36; N, 6.06. Found: C, 67.23; H, 4.58; N, 5.96.
References:
Chakrabarty, Suravi;Monlish, Darlene A.;Gupta, Mohit;Wright, Thomas D.;Hoang, Van T.;Fedak, Mitchel;Chopra, Ishveen;Flaherty, Patrick T.;Madura, Jeffry;Mannepelli, Shankar;Burow, Matthew E.;Cavanaugh, Jane E. [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 13,p. 2294 - 2301] Location in patent:supporting information
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