3,4-dihydro-4,4-diMethyl-7-nitro-naphthalen-1(2H)-one synthesis
- Product Name:3,4-dihydro-4,4-diMethyl-7-nitro-naphthalen-1(2H)-one
- CAS Number:33209-71-1
- Molecular formula:C12H13NO3
- Molecular Weight:219.24
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Yield:33209-71-1 86%
Reaction Conditions:
with sulfuric acid;nitric acid in water at 0 - 10;
Steps:
4,4-Dimethyl-7-nitro-3,4-dihydro-2H-naphthalen-1-one (10)
Concentrated sulfuric acid (165 mL, 3.09 mol) was put into a 500 mL 2-neck flask and cooled to 5-10 °C over an ice / water bath. 4,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one (6) (49.0 mL, 309 mmol) was added slowly, maintaining the solution at 0-10 °C. In a separate 100 mL 2-neck flask, 68.0 - 70.0% nitric acid in water (16.9 mL,) and concentrated sulfuric acid (33.0 mL) were combined and this solution was cooled to 0-10 °C. The nitric/sulfuric acid solution was added to the solution containing (6) dropwise, maintaining the temperature between 0 °C and 10 °C. When the nitric/sulfuric acid solution had all been added the reaction was stirred for 30 minutes, maintaining the temperature at 0-10 °C. The ice water bath was removed and the reaction was allowed to warm to rt while stirring. After most starting material was gone, the reaction was poured onto ice and a precipitate formed, which was filtered off, washed with water and dried by vacuum filtration. The precipitate was triturated with hexane (330 mL) to yield a beige solid (58 g, 86%). LCMS: m/z = 220 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.83 (s, 1H), 8.34 (m, 1H), 7.62 (m, 1H), 2.80 (m, 2H), 2.08 (m, 2H), 1.45 (s, 6H).
References:
Weinberg, Linda R.;Albom, Mark S.;Angeles, Thelma S.;Husten, Jean;Lisko, Joseph G.;McHugh, Robert J.;Milkiewicz, Karen L.;Murthy, Seetha;Ott, Gregory R.;Theroff, Jay P.;Tripathy, Rabindranath;Underiner, Ted L.;Zificsak, Craig A.;Dorsey, Bruce D. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 1,p. 164 - 167] Location in patent:supporting information; experimental part
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