Ammonia → HCID 178508663, compound

HRID 1779278Notes

Reaction equation

HRID 1779278 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]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7847106-Bromo-2,3-dicyanonaphthaleneHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178508663HCID 178508663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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 to 270 ml of absolute methanol in 5 times, and anhydrous ammonia gas was slowly bubbled into the resulting mixture with sufficient stirring 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 filtered and the residue was 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

  1. customprepared
  2. customwas slowly bubbled into the resulting mixture
  3. temperatureThe mixture was refluxed for about 3 hours
  4. customwhile bubbling
  5. temperatureAfter cooling
  6. customthe yellow solid precipitated
  7. filtrationwas filtered
  8. washthe residue was sufficiently washed with methanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b0b2063591954665843292e2c49702a4
Source dataset
uspto-grants-1997_05
Patent number
US05627028

Reaction notes

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