1,10-Phenanthroline → HCID 12994068, compound

HRID 1581753Notes

Reaction equation

HRID 1581753 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH3:15]I.[H-].[Na+].[CH2:19]([C:21]([CH3:23])=[O:22])[CH3:20]>>[CH3:15][O:22][C:21]([C:2]1[CH:3]=[CH:4][C:5]2[C:14](=[C:13]3[C:8](=[CH:7][CH:6]=2)[CH:9]=[CH:10][CH:11]=[N:12]3)[N:1]=1)([CH3:23])[CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 13181,10-PhenanthrolineHCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 24758Sodium hydride

Product 1

HCID 12994068HCID 12994068, compound

Procedure

An embodiment of the above described 2-step process is shown in the following reaction scheme wherein R is hydrogen and 2-[(1-hydroxy-1-methylpropyl)]-1,10-phenanthroline is prepared by coupling methyl ethyl ketone with 1,10-phenanthroline, and the coupling product alkylated with methyl iodide and sodium hydride to form 2-[(1-methoxy-1-methylpropyl)]-1,10-phenanthroline. The latter is reduced with the lanthanideII reducing agent, samarium diiodide, to provide 2-(1-methylpropyl)-1,10-phenanthroline.

Workup

  1. customis shown in the following reaction scheme wherein R
  2. customis prepared

Sources & evidence

ORD record
ord-5c8a663e429145d4b6e363c3ccd922c1
Source dataset
uspto-grants-2004_05
Patent number
US06730788B1

Reaction notes

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