2,4-Dinitrophenol → HCID 22104503, compound

HRID 1457334Notes

Reaction equation

HRID 1457334 reaction equation
[C:1]([C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:18][OH:19])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[K+].[Br-].C1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(O)C=1>C(Cl)Cl.CO>[C:1]([C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH:18]=[O:19])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14932,4-DinitrophenolHCID 253877Potassium BromideHCID 2724130Cornforth reagentHCID 53664777HCID 53664777, compound

Product 1

HCID 22104503HCID 22104503, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. additionwere added
  2. customThe sieves and precipitated salts
  3. customwere then removed by filtration
  4. washthe filtrate washed with water, 5% sodium bicarbonate solution and 1N HCl solution
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a dark brown oil which
  9. customcrystallized
  10. temperatureThe crude product was heated in 1:1/ethyl acetate
  11. additionmethylene chloride with enough methanol added for the crude product
  12. customThe title compound was recrystallized from 1:1/ethyl acetate
  13. customether to yield 0.24 g (24%)

Sources & evidence

ORD record
ord-1a82ce21d71d4adc9409de67d0d30ac0
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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