2,4-Dinitrophenol → HCID 22104503, compound

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Reaction Steps

1.03 g (3.3 mmol) of the title compound of Example 28 was dissolved in 50 ml of methylene chloride at room temperature under a nitrogen atmosphere. 3.76 g (10.0 mmol) of pyridinium dichromate and 4 g powdered 4A molecular sieves were added, and the reaction was allowed to stir at ambient temperature for 3 hours. The sieves and precipitated salts were then removed by filtration and the filtrate washed with water, 5% sodium bicarbonate solution and 1N HCl solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give a dark brown oil which crystallized on standing. The crude product was heated in 1:1/ethyl acetate:methylene chloride with enough methanol added for the crude product to go into solution and decolorized with activated charcoal. The title compound was recrystallized from 1:1/ethyl acetate:ether to yield 0.24 g (24%). TLC: (90:10/CH2Cl2 :MeOH): Rf =0.80. mp=158-160. 1H NMR (CDCl3) δ: 9.42(s); 9.32 (s,1H); 7.32-7.85(m,9H); 4.20-4.50(m,1H); 3.32-3.70(m,2H) 1.70-2.30(m,4H). IR (KBr): 1578, 1590, 1613, 1725 cm-1. Standard Combustion Analysis Calculated: C,74.25; H,5.58; N,4.56. Found: C,73.66; H,5.64; N,4.65. High Resolution Mass Spectrum: m/e=308.1291±0.4 ppm (calculated for C19H18NO3). 2,4-DNP test: positive.

Provenance & Evidence