Tetracyanoquinodimethane → HCID 86741742, compound

HRID 1789279Notes

Reaction equation

HRID 1789279 reaction equation
[CH:1]1[C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9][C:3](=[C:4]([C:7]#[N:8])[C:5]#[N:6])[CH:2]=1.[I-].[CH2:18]([N+:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:19][CH:20]([CH3:22])[CH3:21]>C(#N)C>[CH2:18]([N+:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:19][CH:20]([CH3:22])[CH3:21].[CH:2]1[C:3](=[C:4]([C:5]#[N:6])[C:7]#[N:8])[CH:9]=[CH:10][C:11](=[C:12]([C:13]#[N:14])[C:15]#[N:16])[CH:1]=1

Participants

4

Reactant 2

HCID 73697Tetracyanoquinodimethane2×HCID 143659672-(3-Methylbutyl)isoquinolin-2-ium iodide

Product 1

HCID 86741742HCID 86741742, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
5 °C

Procedure

To 15.3 g of isoamyliodide and 10 g of isoquinoline placed in a four-necked flask equipped with a reflux condenser and mechanical stirrer was added 30 ml of ethanol. The mixture was reacted for 3 hours under reflux. When the reaction was completed, ethanol was removed from the reaction mixture under reduced pressure, the residue was washed 2-times with 45 ml of ethyl ether. 23.0 g of N-isoamylisoquinolinium iodide was obtained as yellow crystals. Subsequently, into a four-necked flask equipped with a reflux condenser and mechanical stirrer was placed 8 g of TCNQ and 280 ml of acetonitrile, and the TCNQ was dissolved in the acetonitrile under reflux. To the flask was added a solution of 9.6 g of N-isoamylisoquinolinium iodide in 40 ml of acetonitrile, and the mixture was reacted for 20 minutes under reflux. The reaction mixture was cooled to 5° C., separated black needles were filtered out and washed 2-times with 100 ml of methanol. 10.4 g of charge transfer complex of N-isoamylisoquinolinium TCNQ was obtained. The infra-red spectrum of the complex was shown in FIG. 3. The specific resistance of the complex measured by the same method as that described in Example 1 was 3.6 Ωcm.

Workup

  1. customSubsequently, into a four-necked flask equipped with a reflux condenser and mechanical stirrer
  2. temperatureunder reflux
  3. customthe mixture was reacted for 20 minutes
  4. temperatureunder reflux
  5. customseparated black needles
  6. filtrationwere filtered out
  7. washwashed 2-times with 100 ml of methanol

Sources & evidence

ORD record
ord-bb97313df20841e593595712f8498a7c
Source dataset
uspto-grants-1987_08
Patent number
US04688153

Reaction notes

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