Ammonia → HCID 178508665, compound

HRID 579722Notes

Reaction equation

HRID 579722 reaction equation
[C:1]([C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)#[N:2].[NH3:15].C[O-].[Na+]>CO>[NH:14]=[C:13]1[C:12]2[CH:11]=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][C:3]=2[C:1](=[NH:15])[NH:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6012702,3-DicyanonaphthaleneHCID 10942334Sodium Methoxide

Product 1

HCID 178508665HCID 178508665, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

That is, α,α,α',α'-tetrabromo-o-xylene [the formula (V)] in an amount of 0.1 mol and fumaronitrile in an amount of 0.178 mol are reacted at 75° C. for 7 hours in the presence of 0.67 mol of sodium iodide in anhydrous N,N-dimethylformamide to yield 2,3-dicyanonaphthalene of the formula (VI). Subsequently, 57.3 mmol of the 2,3-dicyanonaphthalene is reacted with ammonia in the presence of sodium methoxide in methanol with heating for 3 hours to yield 1,3-diiminobenzo(f)isoindoline of the formula (VII). Further, 30.6 mmol of the 1,3-diiminobenzo(f)isoindoline was reacted with 47.1 mmol of silicon tetrachloride in anhydrous tetralin and anhydrous tri-n-butyl-amine under reflux for about 3 hours to give dichlorosilicon naphthalocyanine [SiNoX2 (X=Cl)] which can be represented by the formula (II) except that the two OHs are replaced by two Cl's. Then, this compound is treated with concentrated sulfuric acid and then concentrated ammonia water to give dihydroxysilicon naphthalocyanine [SiNcX2 (X=OH)] of the formula (II).

Workup

  1. temperaturewith heating for 3 hours

Sources & evidence

ORD record
ord-392ca5b318a24345ac7c72f2ba8a818c
Source dataset
uspto-grants-1988_06
Patent number
US04749637

Reaction notes

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