Benzyl Bromide → 5-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carbonitrile

HRID 1811422Notes

Reaction equation

HRID 1811422 reaction equation
[O:1]=[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[CH:8]=[C:7]([C:16]#[N:17])[CH:6]=[CH:5][C:4]=2[NH:3]1.[H-].[Na+].[H][H].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([N:3]1[C:2](=[O:1])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[CH:8]=[C:7]([C:16]#[N:17])[CH:6]=[CH:5][C:4]1=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 167280326-oxo-5H-phenanthridine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 665968095-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carbonitrileYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Oxo-5,6-dihydrophenanthridine-2-carbonitrile (1 g) was suspended in DMF (20 ml), 60% sodium hydride (0.2 g) was added under ice cooling, and stirring was carried out until the generation of hydrogen stopped. Benzyl bromide (0.59 ml) was added, followed by stirring at room temperature for 1 hour. Water was added, and the produced solid was collected by filtration and purified by silica gel chromatography (dichloromethane:n-hexane=1:1) to thereby obtain 0.68 g (yield: 48%) of the title compound as colorless crystals.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. filtrationthe produced solid was collected by filtration
  3. custompurified by silica gel chromatography (dichloromethane:n-hexane=1:1)

Sources & evidence

ORD record
ord-d71381e23ccf428daccc073d443b015e
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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