Selenium Dioxide → 5-Cyano-[1,2]naphthoquinone

HRID 719166Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13])#[N:2].[Se](=O)=[O:15]>>[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:15])[C:8]2=[O:13])#[N:2]

Participants

Reactant 2

HCID 24007Selenium Dioxide

HCID 109318735-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 218968265-Cyano-[1,2]naphthoquinone

Procedure

Treatment of 5-cyano-1-tetralone with selenium dioxide as described in Reference Example 1A yielded the corresponding 5-cyano-[1,2]naphthoquinone, which was coupled with 2,3-diamino-benzoic acid, diacetate salt, as described to yield the title compound.

Sources & evidence

ORD record: ord-714770681b044171834b755bc176dd89
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132419B2

Reaction notes

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