Ethanol → HCID 54417824, compound

HRID 2251940Notes

Reaction equation

HRID 2251940 reaction equation
O=[C:2]1[C:11]2[C:6]3[C:7](=[CH:12][CH:13]=[CH:14][C:5]=3[C:4](=O)[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:8]=[CH:9][CH:10]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C>C1COCC1>[CH2:2]1[C:11]2[C:6]3[C:7](=[CH:12][CH:13]=[CH:14][C:5]=3[CH2:4][N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 11623143HCID 11623143, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54417824HCID 54417824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (18.6 mmol) 4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-butylamine are dissolved in 200 ml THF and 6.1 g (160.7 mmol) LiAlH4 are added in portions under cooling. The suspension is stirred for 24 hours at RT and for 8 hours under reflux. After cooling, ethanol is carefully added dropwise until no more foam appears. The mixture is filtered and the filtrate is concentrated under vacuum. The residue is distributed between chloroform and water. The organic phase is dried over sodium sulfate and, after withdraw of the solvent, chromatographically purified over silica gel with CHCl3/CH3OH/NH4OH (90/10/0.5 to 90/10/1): Yield 2.2 g (49%).

Workup

  1. temperatureunder cooling
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated under vacuum
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customafter withdraw of the solvent
  8. customchromatographically purified over silica gel with CHCl3/CH3OH/NH4OH (90/10/0.5 to 90/10/1)

Sources & evidence

ORD record
ord-f468d340df2943e98a80abfe913fb672
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

Loading…