Picolinic acid → HCID 86584704, compound

HRID 1362789Notes

Reaction equation

HRID 1362789 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].[Ir:10](Cl)(Cl)Cl.[C:14]1([C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=[O:8].[Ir+3:10].[C:14]1([C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:14]1([C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=[O:8].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 1018Picolinic acidHCID 86584703HCID 86584703, compound

Product 1

HCID 86584704HCID 86584704, compoundYield 229.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.14 mmol (0.26 g) of picolinic acid was added to a room-temperature solution of 0.80 mmol 2-phenylbenzothiazole Iridium chloride dimer (1.0 g) in 60 mL of dichloromethane. The mixture was heated to reflux under nitrogen in an oil bath for 8.5 hours. The reaction mixture was cooled to room temperature, and the yellow precipitate was filtered off via vacuum. The filtrate was concentrated and methanol was added to precipitate more product. Successive filtrations and precipitations yielded about 900 mg of impure product. Emission spectrum is in FIG. 45.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen in an oil bath for 8.5 hours
  3. filtrationthe yellow precipitate was filtered off via vacuum
  4. concentrationThe filtrate was concentrated
  5. additionmethanol was added
  6. customto precipitate more product
  7. filtrationSuccessive filtrations and precipitations

Sources & evidence

ORD record
ord-d56fc11d68904dc58f441dbaa8fda148
Source dataset
uspto-grants-2011_02
Patent number
US07883787B2

Reaction notes

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