Ammonia → HCID 178508665, compound

HRID 2082274Notes

Reaction equation

HRID 2082274 reaction equation
[Na].C[O-].[Na+].[C:5]([C:7]1[C:16]([C:17]#[N:18])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)#[N:6].[NH3:19]>CO>[NH:18]=[C:17]1[C:16]2[CH:15]=[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[CH:8][C:7]=2[C:5](=[NH:19])[NH:6]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6012702,3-DicyanonaphthaleneHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178508665HCID 178508665, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, in an atmosphere of nitrogen, 0.64 g (28 mmoles) of metallic sodium was added in five portions to 90 ml of anhydrous methanol to prepare a methanolic solution of sodium methoxide. To the methanolic solution was added 10.2 g (57.3 mmoles) of 2,3-dicyanonaphthalene. While thoroughly stirring the mixture, anhydrous ammonia gas was bubbled into the mixture slowly over a period of about one hour at room temperature. Then, the mixture was heated under reflux for about 3 hours while bubbling anhydrous ammonia gas. After cooling the mixture, the deposited yellow-colored solid product was collected by filtration, thoroughly washed with methanol and dried in vacuum. Thus, about 9.5 g (86%) of 1,3-diiminobenzo(f)isoindoline was obtained as a yellow colored solid. It was used in the subsequent reaction without purification.

Workup

  1. customwas bubbled into the mixture slowly over a period of about one hour at room temperature
  2. temperatureThen, the mixture was heated
  3. temperatureunder reflux for about 3 hours
  4. customwhile bubbling anhydrous ammonia gas
  5. temperatureAfter cooling the mixture
  6. filtrationthe deposited yellow-colored solid product was collected by filtration
  7. washthoroughly washed with methanol
  8. customdried in vacuum

Sources & evidence

ORD record
ord-e43e36affc8e473ebb08109844368d93
Source dataset
uspto-grants-1993_02
Patent number
US05188922

Reaction notes

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