3'-Chloropropiophenone → HCID 19922822, compound

HRID 1647390Notes

Reaction equation

HRID 1647390 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].Cl[C:13]1[CH:14]=[C:15]([C:19](=O)[CH2:20][CH3:21])[CH:16]=[CH:17][CH:18]=1>>[C:15]1([C:19]2[C:5]3[C:6](=[C:7]4[C:8](=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:13][CH:14]=3)=[CH:20][CH:21]=[N:10]4)[N:11]=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 5871283'-ChloropropiophenoneHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 19922822HCID 19922822, compoundYield 15%

Procedure

In another approach illustrated in FIG. 21 the inventors performed a double Skraup reaction between 4-nitro-o-phenylenediamine 60 and two molecules of 3'-chloropropiophenone 61 to afford in ca. 15% yield 4,7-diphenyl-5-nitro-1,10-phenanthroline 62. Specifically, 4-Nitro-o-phenylenediamine 60 was reacted with β-chloropropiophenone 61 under the Skraup reaction conditions to afford in 15% compound 62, which was analyzed and found to have the following physical characteristics:

Sources & evidence

ORD record
ord-09c8354f63354125b92d9bf2c9556ee2
Source dataset
uspto-grants-1995_07
Patent number
US05432172

Reaction notes

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