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

HRID 1983965ノート

反応式

HRID 1983965 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-25df7fc1a05d45788fd7c453fa35d602
出典データセット
uspto-grants-2009_06
特許番号
US07544215B2

反応ノート

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