2,3-Dichloroquinoxaline → 2-benzyl-3-chloroquinoxaline

HRID 1783377Notes

Reaction equation

HRID 1783377 reaction equation
[CH2:1]([C:8]1[C:17](C#N)=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20]C1C(Cl)=NC2C(=CC=CC=2)N=1.C1C=CC2C(=NC3C(N)=NNC=3N=2)C=1.C([Mg]Cl)C1C=CC=CC=1>C1COCC1>[CH2:1]([C:8]1[C:17]([Cl:20])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 166592,3-DichloroquinoxalineHCID 57590379HCID 57590379, compoundHCID 178418336HCID 178418336, compoundHCID 178509214HCID 178509214, compound

Product 1

HCID 4888112-benzyl-3-chloroquinoxaline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 3 can be prepared from the starting material 2,3-dichloroquinoxaline 1 following the reaction in Scheme 1. In this manner, quinoxaline 1 can be reacted with benzylmagnesium chloride in THF to afford 2-benzyl-3-chloroquinoxaline 2. 2-Benzylquinoxalines can also be prepared by reaction with alternative alkylating reagents, such as, but not limited to, benzyllithium. 2-Benzyl-3-chloroquinoxaline 2 can be reacted with cyanide to obtain intermediate 2-benzyl-3-cyanoquinoxaline 3.

Workup

  1. customthe reaction in Scheme 1

Sources & evidence

ORD record
ord-39b98bd20bf342e696ee6a5bad97b8d0
Source dataset
uspto-grants-2009_03
Patent number
US07501416B2

Reaction notes

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