2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 66815199, compound

HRID 448167Notes

Reaction equation

HRID 448167 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1)#[N:3].[C:12]([O-])(=O)[CH3:13].[Na+].[C:17]([C:19]1C(=O)[C:24](Cl)=[C:23](Cl)[C:21](=O)[C:20]=1C#N)#[N:18]>>[NH:18]1[C:21]2=[C:23]3[C:24](=[CH:12][CH:13]=[C:20]2[CH:19]=[CH:17]1)[C:8]1[C:7](=[CH:6][CH:5]=[C:4]([C:2]#[N:3])[CH:9]=1)[NH:10]3

Participants

4

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 517045Sodium AcetateHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 66815199HCID 66815199, compoundYield 93.3%

Procedure

4-cyanophenylhydrazine hydrochloride (1.36 g; 8.0 mmol), sodium acetate (656 mg; 8.0 mmol); stage B: DDQ (545 mg; 2.40 mmol); stage C: chromatography on silica gel (from 9/1 to 7/3 cyclohexane/EtOAc) allows isolation of the expected compound (517 mg; 2.24 mmol; yield=56%) in the form of a beige-colored solid.

Sources & evidence

ORD record
ord-c18b58915db645bd99224383a7621419
Source dataset
uspto-grants-2013_07
Patent number
US08481586B2

Reaction notes

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