Ammonia → HCID 178508663, compound

HRID 1755702Notes

Reaction equation

HRID 1755702 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-7546540cbf5e4b7793864c8c20e27222
Source dataset
uspto-grants-1995_08
Patent number
US05438135

Reaction notes

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