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

HRID 1881216ノート

反応式

HRID 1881216 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 86633446HCID 86633446、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ef1a3079441b41da83ce2fad7cbe8a8c
出典データセット
uspto-grants-2012_11
特許番号
US08318785B2

反応ノート

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