N-bromobutanimide → 3-Hydroxy-6-nitroisobenzofuran-1(3h)-one

HRID 280841

反応式

HRID 280841 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1C(=[O:20])CCC1=O>C(Cl)(Cl)(Cl)Cl>[OH:20][CH:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:10](=[O:13])[O:9]1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 2235846-Nitrophthalide

生成物 1

HCID 5226713-Hydroxy-6-nitroisobenzofuran-1(3h)-one

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 6-nitro-1(3H)-isobenzofuranone (8.99 g, 50.0 mmol) and N-bromosuccinimide (8.9 g, 50.0 mmol) in carbon tetrachloride (135 mL) was stirred and heated under reflux for one hour during which time the reaction mixture was exposed to the light from a 275 Watt, 125 Volt Hanovia sunlamp that was situated 8 inches from the flask. After cooling, the succinimide was removed by filtration, and the filtrate was evaporated in vacuo. The oily residue was mixed with water (200 mL), and the mixture was refluxed for one hour to give a clear, colorless solution. On cooling, the Compound 3a crystallized from solution. An analytical sample was prepared by recrystallization from water; m.p. 157°-160° C.; IR 3390 cm-1 (OH), 1770 cm-1 (C=O), 1H NMR (CDCl3 -Me2SO-d6 -D2O) δ6.78 (s, br, 1H, H3), 7.88 (d, 1H, H4, J4,5 =9 Hz), 8.56 (d, 1H, H5, J=9 Hz), 8.62 (s, 1H, H6).

後処理

  1. temperatureheated
  2. temperatureunder reflux for one hour during which time the reaction mixture
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. additionThe oily residue was mixed with water (200 mL)
  7. temperaturethe mixture was refluxed for one hour
  8. customto give a clear, colorless solution
  9. temperatureOn cooling
  10. customthe Compound 3a crystallized from solution
  11. customAn analytical sample was prepared by recrystallization from water

出典と根拠

ORDレコード
ord-1922f23bade84f599a4681be49eeba44
出典データセット
uspto-grants-1986_05
特許番号
US04591587

関連ノート

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