Ammonia → HCID 178508663, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:13])[C:6]([C:14]#[N:15])=[CH:5]2.C[O-].[Na+].[Na].[NH3:20]>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2=[CH:8][C:7]3[C:12](=[NH:13])[NH:15][C:14](=[NH:20])[C:6]=3[CH:5]=[C:4]2[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under nitrogen, 44.1 g (0.17 mol) of 6-bromo-2,3-dicyanonaphthalene was added to a solution of sodium methoxide in methanol prepared by adding 1.92 g (84 mmols) of metallic sodium in 5 times to 270 ml of absolute methanol, and anhydrous ammonia gas was slowly bubbled into the resulting mixture with sufficient mixing at room temperature for about 1 hour. The mixture was refluxed for about 3 hours, while bubbling therethrough anhydrous ammonia gas. After cooling, the yellow solid precipitated was collected by filtration, sufficiently washed with methanol and dried under reduced pressure to obtain 45 g of 6-bromo-1,3-diiminobenz[f]isoindoline as a yellow solid. IR spectrum of this 6-bromo-1,3-diiminobenz[f]isoindoline is shown in FIG. 4. The 6-bromo-1,3-diiminobenz[f]isoindoline was used in the subsequent reaction without further purification.
Workup
- customprepared
- customwas slowly bubbled into the resulting mixture
- additionwith sufficient mixing at room temperature for about 1 hour
- temperatureThe mixture was refluxed for about 3 hours
- customwhile bubbling
- temperatureAfter cooling
- customthe yellow solid precipitated
- filtrationwas collected by filtration
- washsufficiently washed with methanol
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-fbbbcf9d192b4383aa81762b2f285be0
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05110968
Reaction notes
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