Nitric Acid → HCID 58979967, compound

HRID 1180681Notes

Reaction equation

[C:1]1([C:7]2[O:11][C:10]([C:12]3[CH:25]=[CH:24][C:23]4[C:14](=[C:15]5[C:20](=[CH:21][CH:22]=4)[CH:19]=[CH:18][C:17]([C:26]4[O:27][C:28]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=6)=[N:29][N:30]=4)=[N:16]5)[N:13]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+]([O-])(O)=O.[Br-].[K+].[OH-:48].[Na+].[OH2:50]>C(Cl)Cl>[C:31]1([C:28]2[O:27][C:26]([C:17]3[CH:18]=[CH:19][C:20]4[C:21](=[O:48])[C:22](=[O:50])[C:23]5[C:14](=[N:13][C:12]([C:10]6[O:11][C:7]([C:1]7[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=7)=[N:8][N:9]=6)=[CH:25][CH:24]=5)[C:15]=4[N:16]=3)=[N:30][N:29]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a 100 ml one-necked flask was added a mixture of 4 g (0.008 mol) 2,9-bis-(5-phenyl-[1,3,4]oxadiazol-2-yl)-[1,10]phenanthroline and 15.3 ml sulfuric acid (concentrate). The mixture was subsequently iced and 15.3 ml HNO3 was added into the iced mixture drop by drop. Next, 1.5 g (0.013 mol) potassium bromide was added to the iced mixture, and then the mixture solution was heated to 40° C. and stirred overnight. After completion of reaction, as shown in Scheme 3, the reaction mixture was placed into 200 ml iced water, and then NaOH(aq) was added to adjust pH value to a range from 5 to 6. Next, 150 ml CH2Cl2 was subsequently added. The organic layer was separated, dehydrated by MgSO4, concentrated, and purified by column chromatography to obtain white products 2,9-bis-(5-phenyl-[1,3,4]oxadiazol-2-yl)-[1,10]phenanthroline-5,6-dione 0.8 g (0.0016 mol, yield 20%).

Workup

additionTo a 100 ml one-necked flask was added
customAfter completion of reaction
customThe organic layer was separated
concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-4008ea3e0dba4292bbdceeef0e80ef69
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282586B1

Reaction notes

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