Ammonia → HCID 178508663, compound

HRID 249532Notes

Reaction equation

HRID 249532 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 (0.172 mol) of 6-bromo-2,3-dicyanonaphthalene was added to a solution of sodium methoxide in methanol prepared by adding 1.92 g (84 m mols) of metallic sodium to 270 ml of absolute methanol, and anhydrous ammonia gas was slowly bubbled into the resulting mixture 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 for about 1 hour
  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-3bbd221ac8ed4df29827e0004fb45330
Source dataset
uspto-grants-1993_05
Patent number
US05214188

Reaction notes

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