2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 8-cyano-2-naphthoate

HRID 376805Notes

Reaction equation

HRID 376805 reaction equation
[C:1]([C:3]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH:4]=1)#[N:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8]2)#[N:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14756558Methyl 8-cyano-5,6-dihydro-2-naphthoate

Product 1

HCID 14756562Methyl 8-cyano-2-naphthoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The remaining naphthoate (11) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dioxane to aromatize the adjacent ring to give the methyl 8-cyano-2-naphthoate (13). Then, the nitrile was reduced via hydrogentation and the methyl ester saponified to the carboxylic acid. This acid was then N-BOC-protected to give N-(BOC)-8-aminomethyl-2-naphthoic acid (14) as an intermediate for incorporation into the cyclic peptide.

Sources & evidence

ORD record
ord-551c169e615b434cbf68d656ac6975ce
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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