Ethanol, 1-bromo- → HCID 178518385, compound

HRID 1983963Notes

Reaction equation

HRID 1983963 reaction equation
[Br:1][CH:2]([OH:4])[CH3:3].[N:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[N:12]/[C:13]2[CH:14]=[CH:15][C:16]3[C:17](=[O:27])[NH:18][C:19](=[O:26])[C:20]4[C:25]=3[C:24]=2[CH:23]=[CH:22][CH:21]=4)=[CH:7][CH:6]=1>C(#N)C.CC(C)=O>[Br-:1].[O:26]=[C:19]1[C:20]2[C:25]3[C:24](=[C:13](/[N:12]=[CH:11]/[C:8]4[CH:9]=[CH:10][N+:5]([CH2:3][CH2:2][OH:4])=[CH:6][CH:7]=4)[CH:14]=[CH:15][C:16]=3[C:17](=[O:27])[NH:18]1)[CH:23]=[CH:22][CH:21]=2

Participants

5

Reactant 2

HCID 14202443Ethanol, 1-bromo-HCID 178518384HCID 178518384, compound

Product 1

HCID 178518385HCID 178518385, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

2.34 g (18.75 mmol) of bromoethanol was added dropwise to a solution of 1.13 g (3.75 mmol) of 6-{[(E)-4-pyridinylmethylidene]amino}-1H-benzo[de]isoquinolin-1,3(2H)-dione in 60 mL of acetonitrile or acetone and the solution was then heated at reflux for 1 hour. After concentration to about ⅓ of the amount of solvent and cooling to room temperature, the resulting precipitate was suction-filtered off, washed with ethyl acetate and dried under vacuum. Yield: 0.59 g (37% of the theoretical), dark-yellow powder. 1H-NMR (d6-DMSO/300 MHz): δ=3.58 (t, J=13.5 Hz, 2H, ethyl); 4.01 (t, J=13.5 Hz, 2H, ethyl); 6.45 (s, 1H); 7.54-7.58 (m, 2H, aromatic); 7.19 (d, J=5.8 Hz, 2H, pyridyl); 8.40 (m, 1H, aromatic); 8.63 (d, J=5.8 Hz, 2H, pyridyl); 8.72-8.75 (m, 2H, aromatic); 11.39 (s, 1H, N—H).

Workup

  1. temperaturethe solution was then heated
  2. temperatureat reflux for 1 hour
  3. concentrationAfter concentration to about ⅓ of the amount of solvent
  4. filtrationthe resulting precipitate was suction-filtered off
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c8e24b23fe5b44f3bf548bd9fff81f61
Source dataset
uspto-grants-2009_06
Patent number
US07544215B2

Reaction notes

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