Pyridine → 5,6-Dihydroxy-4,7-dinitro-2-benzofuran-1(3H)-one

HRID 1881216Notes

Reaction equation

HRID 1881216 reaction equation
[OH:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[O:11]C)[C:7](=[O:16])[O:6][CH2:5]2.[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1>C(OCC)(=O)C>[OH:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[OH:11])[C:7](=[O:16])[O:6][CH2:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 86633446HCID 86633446, compound

Product 1

HCID 159832325,6-Dihydroxy-4,7-dinitro-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Hydroxy-6-methoxy-4,7-dinitro-3H-isobenzofuran-1-one (210 mg) was dissolved in ethyl acetate (2.5 ml) followed by addition of aluminum chloride (132 mg) in nitrogen atmosphere. Pyridine (265 μl, 3.28 mmol) was added dropwise. The resulting mixture was heated to reflux for 2 hours, and then quenched with water (0.5 ml) and conc. HCl (0.5 ml) at 75° C. Ethyl acetate (15 ml) was added and phases were separated. The aqueous layer was extracted once with ethyl acetate (15 ml). The combined organic layers were dried over anhydrous Na2SO4. The product was filtrated, evaporated to dryness and recrystallized from heptane-toluene-ethyl acetate.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customquenched with water (0.5 ml) and conc. HCl (0.5 ml) at 75° C
  4. additionEthyl acetate (15 ml) was added
  5. customphases were separated
  6. extractionThe aqueous layer was extracted once with ethyl acetate (15 ml)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. filtrationThe product was filtrated
  9. customevaporated to dryness
  10. customrecrystallized from heptane-toluene-ethyl acetate

Sources & evidence

ORD record
ord-ef1a3079441b41da83ce2fad7cbe8a8c
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

Loading…