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1,10-Phenanthroline → 1-Oxo-2,6-diphenyl-1lambda~5~-pyridine

HRID 1848951
Notes
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Reaction equation

HRID 1848951 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1[C:21]2[C:12](=[CH:13][CH:14]=[C:15]3[C:20]=2N=CC=C3)C=CC=1.[N+:22]1([O-:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[Li])(C)(C)C>C(OCC)(=O)C.[Cu]I.CO.CN1C(=O)N(C)CCC1>[C:2]1([C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([C:12]3[CH:21]=[CH:20][CH:15]=[CH:14][CH:13]=3)[N+:22]=2[O-:28])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 12753Pyridine N-OxideHCID 178506942HCID 178506942, compound

Product 1

HCID 127251411-Oxo-2,6-diphenyl-1lambda~5~-pyridineYield 202.2%

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 887MethanolSolvent
HCID 8857Ethyl AcetateSolvent2×
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

Copper(I) iodide (19 mg, 0.1 mmol), iodobenzene (408 mg, 2.0 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol), pyridine N-oxide (95 mg, 1.0 mmol), t-BuOLi (145 mg, 1.8 mmol), and anhydrous DMPU (0.5 mL), 125° C., 1 hour. After column chromatography (ethyl acetate, then 15% MeOH in ethyl acetate) 50 mg of 2,6-diphenylpyridine 1-oxide (20%) was obtained as an off-white solid. Additionally, 2-phenylpyridine 1-oxide (100 mg, 58%) was obtained as a colorless solid. These compounds are known.7,12 2-Phenylpyridine 1-oxide: Rf=0.46 (3/7 methanol/ethyl acetate). The molecule structure of 2-phenylpyridine 1-oxide and its 1H NMR spectrum are shown in FIG. 59. 1H NMR (300 MHz, CDCl3) δ 7.17-7.34 (m, 2H), 7.38-7.53 (m, 4H), 7.80 (dd, J=7.7 Hz, 1.7 Hz, 2H), 8.33 (d, J=6.0 Hz, 1H). 2,6-Diphenylpyridine 1-oxide: Rf=0.30 (1/1 ethyl acetate/hexanes). 1H NMR (300 MHz, CDCl3) δ 7.28-7.52 (m, 9H), 7.80-7.87 (m, 4H).

Sources & evidence

ORD record
ord-1617b7b0216e42a492879f70aad26585
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952207B2

Reaction notes

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