3-nitrofluoren-9-one synthesis
- Product Name:3-nitrofluoren-9-one
- CAS Number:42135-22-8
- Molecular formula:C13H7NO3
- Molecular Weight:225.2
124391-60-2
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Yield:42135-22-8 91%
Reaction Conditions:
with polyphosphoric acid at 90 - 165; for 6 h;Friedel-Crafts Acylation;
Steps:
3-Nitro-9H-fluoren-9-one (4c)4
5-Nitrobiphenyl-2-carboxylic acid (3c, 2.43 g, 10.0 mmol) was added to stirred polyphosphoric acid (PPA, 36 g) at 90 - 100 °C. The resulting yellow mixture was heated for 6 h at 160 - 165 °C. The green reaction mixture was cooled to 40 - 50 °C and poured into cold (0 - 5 °C) aqueous NaOH (10%, 250 mL). A dark yellow precipitate was formed and filtered off. It was thouroughly washed with H2O and dried at 60°C. The raw material (2.2 g) was dissolved in warm MeCN (400 mL), filtered through a plug of celite. The yellow filtrate was evaporated to 40 mL to give the title compound 4c (2.05 g, 9.1 mmol, 91% yield, Rf = 0.54, cyclohexane/CHCl3, 1:3) as gold-yellow needles. 1H NMR (300 MHz, CDCl3) δH 8.33 (d, J = 1.8 Hz, 1HAr, 4-H), 8.18 (dd, J = 8.1, 1.9 Hz, 1HAr, 2-H), 7.80 (d, J = 8.1 Hz, 1HAr, 1-H), 7.75 (d, J = 7.4 Hz, 1HAr, 8-H), 7.66 (dt, J = 7.0, 0.9 Hz, 1HAr, 5-H), 7.61 (td, J = 7.4, 1.2Hz, 1HAr, 6-H), 7.42 (td, J = 7.4, 1.3 Hz, 1HAr, 7-H). 13C NMR (75 MHz, CDCl3) δC 145.94 (1CAr, 5a-C), 142.70 (1CAr, 4a-C), 138.59 (1CAr, 9a-C), 135.78 (1CArH, 6-C), 134.43 (1CAr, 8a-C), 130.67 (1C ArH, 8-C), 125.16, 124.91 and 124.83 (3CArH, 7-C, 1-C, 2-C), 121.36 (1CArH, 5-C), 115.47 (1CArH, 4-C); Signals for two carbons (C=O, 3-C) could not be observed, due to low solubility in CDCl3.
References:
Teodoro, Rodrigo;Scheunemann, Matthias;Wenzel, Barbara;Peters, Dan;Deuther-Conrad, Winnie;Brust, Peter [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 9,p. 1471 - 1475] Location in patent:supporting information
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42135-22-8
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![[1,1'-Biphenyl]-2-carboxamide, N-methyl-5-nitro-](/CAS/20210305/GIF/1166974-87-3.gif)
1166974-87-3
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42135-22-8
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