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

HRID 504013Notes

Reaction equation

HRID 504013 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-09ccd191e6f040f69082cf501e9f2613
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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