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

HRID 1983965Notes

Reaction equation

HRID 1983965 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-25df7fc1a05d45788fd7c453fa35d602
Source dataset
uspto-grants-2009_06
Patent number
US07544215B2

Reaction notes

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