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

HRID 280707

반응식

HRID 280707 반응식
[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

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 2235846-Nitrophthalide

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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=0), 1H NMR (CDCl3 -Me2SO-d6 -D2O)δ6.78 (s, br, 1H, H3), 7.88 (d, 1H, H4, J 4,5 =9 Hz), 8.56 (d, 1H, H5, J=9 Hz), 8.62 (s, 1H, H6).

후처리

  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

출처 및 근거

ORD 기록
ord-4232bad59399424d88413d8223966622
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590276

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