Potassium Carbonate → 1-pyridin-2-yl-10H-phenoxazine

HRID 348385

Reaction equation

HRID 348385 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:11]1[C:12]2[NH:13][C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[O:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 67278PhenoxazineHCID 2211262-Iodopyridine

Product 1

HCID 221462711-pyridin-2-yl-10H-phenoxazineYield 91%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

To start with, 1.73 g of phenoxazine, 2.90 g of 2-iodopyridine, 5.24 g of potassium carbonate, 1.2 g of copper powder, and 0.25 g of 18-crown-6-ether were mixed with the use of 20 ml of ortho-dichlorobenzene as a solvent, followed by reflux under a nitrogen atmosphere for 8 hours. After that, copper and inorganic salt were removed, and then column purification using a dichloromethane solvent was performed to give a ligand ppx (1-(2-pyridyl)phenoxazine) (white powder; yield: 91%). A summary of the synthesis scheme is shown in the following (a-2).

Workup

  1. temperatureby reflux under a nitrogen atmosphere for 8 hours
  2. customAfter that, copper and inorganic salt were removed
  3. customcolumn purification

Sources & evidence

ORD record
ord-072d83ded91b4c3898ba0f2abf80ddac
Source dataset
uspto-grants-2007_02
Patent number
US07176307B2

Linked notes

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