Hydrochloric Acid → HCID 23144899, compound

HRID 1820568Notes

Reaction equation

HRID 1820568 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Ir:38].Cl>OCC(CO)O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Ir+3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1378821-PhenylisoquinolineHCID 5380024HCID 5380024, compound

Product 1

HCID 23144899HCID 23144899, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
135 °C

Procedure

50 ml of glycerol was introduced into a 100 ml-four-neck flask, and then stirred and heated at 130 to 140° C. for 2 hours while bubbling with nitrogen gas. The glycerol was left to cool to 100° C., and then 1.03 g (5.02 mmol) of 1-phenylisoquinoline and 0.50 g (1.02 mmol) of iridium (III) acetylacetonate were added. The reaction mixture was stirred and heated for 7 hours at around 210° C. under a nitrogen gas flow. After being left to cool to room temperature, the reaction product was added to 300 ml of 1N-hydrochloric acid, and the resulting precipitate was filtered and then washed with water. The precipitate was purified using silica gel column chromatography with chloroform used as an eluent, to yield 0.22 g of a red powder of iridium (III) tris(1-phenylisoquinoline) (26.8% yield). FIG. 1 illustrates the crystal structure of the iridium (III) tris(1-phenylisoquinoline) as obtained from single crystal structure analysis. As can be seen from FIG. 1, this crystal had pores with a diameter of about 0.8 nm.

Workup

  1. customwhile bubbling with nitrogen gas
  2. waitThe glycerol was left
  3. temperatureto cool to 100° C.
  4. stirringThe reaction mixture was stirred
  5. temperatureheated for 7 hours at around 210° C. under a nitrogen gas flow
  6. waitAfter being left
  7. temperatureto cool to room temperature
  8. filtrationthe resulting precipitate was filtered
  9. washwashed with water
  10. customThe precipitate was purified

Sources & evidence

ORD record
ord-1219abe8d2034eb4b48482e33ecb0d14
Source dataset
uspto-grants-2009_10
Patent number
US07604683B2

Reaction notes

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