Phosphorus tribromide → 2-{4-[(2-bromoethyl)(ethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3-(2H)-dione

HRID 1983965노트

반응식

HRID 1983965 반응식
[CH2:1]([N:3]([CH2:28][CH2:29]O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([N+:24]([O-:26])=[O:25])=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[C:11]2=[O:27])=[CH:6][CH:5]=1)[CH3:2].P(Br)(Br)[Br:32]>C(Cl)(Cl)Cl>[Br:32][CH2:29][CH2:28][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([N+:24]([O-:26])=[O:25])=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[C:11]2=[O:27])=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 24614Phosphorus tribromideHCID 866134062-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3(2H)-dione

생성물 1

HCID 866134072-{4-[(2-bromoethyl)(ethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3-(2H)-dione

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

1.5 g (3.7 mmol) of 2-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-6-nitro-1H-benzo[de]isoquinolin-1,3(2H)-dione was dissolved in 80 mL of chloroform and heated to a boil. Then, 10.7 mL (11.1 mmol) of phosphorus tribromide was added dropwise within 20 minutes, and the solution was heated at reflux for an additional 2 hours. The mixture was then poured onto ice, and the aqueous phase was extracted with chloroform. The combined organic phases were dried over magnesium sulfate. The purification was performed by column chromatography on silica gel with toluene as the developing solvent. Yield: 0.90 g (52% of the theoretical), dark-red powder. 1H-NMR (d6DMSO/300 MHz): δ=1.12 (t, J=8.1 Hz, 3H), 1.86 (q, 2H), 3.58 (t, J=6.9 Hz, 2H), 4.01 (t, J=6.9 Hz, 2H), 6.96 (d, J=4.2 Hz, 2H, phenyl), 7.83 (d, J=7.6 Hz, 1H, naphthalene), 7.95 (d, J=4.4 Hz, 2H, phenyl), 8.33 (d, J=8.1 Hz, 1H, naphthalene), 8.52 (d, J=8.8 Hz, 1H, naphthalene), 8.67 (d, J=8.0 Hz, 1H, naphthalene), 9.13 (d, J=8.6 Hz, 1H, naphthalene).

후처리

  1. temperatureheated to a boil
  2. temperaturethe solution was heated
  3. temperatureat reflux for an additional 2 hours
  4. additionThe mixture was then poured onto ice
  5. extractionthe aqueous phase was extracted with chloroform
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customThe purification

출처 및 근거

ORD 기록
ord-25df7fc1a05d45788fd7c453fa35d602
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544215B2

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