Toluene → 3-chloro-1H-quinoxalin-2-one

HRID 882859

Reaction equation

HRID 882859 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3](=[O:11])[C:2]1=O.O=S(Cl)[Cl:15].C1(C)C=CC=CC=1>CN(C=O)C>[Cl:15][C:2]1[C:3](=[O:11])[NH:4][C:5]2[C:10]([N:1]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 274912,3-Dihydroxyquinoxaline

Product 1

HCID 3027053-chloro-1H-quinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The quinoxalin-2-one of the present example is prepared with phenyl-1,2-diamine and oxalic acid via the method described in Example 12 to afford the 1,4-Dihydro quinoxaline-2,3-dione. The 1,4-Dihydro quinoxaline-2,3-dione is then treated with SOCl2 in 2.5% DMF:toluene, heated to 130° C., stirred for 2 h, filtered and concentrated to afford the 3-chloro-1H-quinoxalin-2-one in crude form.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-031c6e8730de4d5a887aa11efd4b647c
Source dataset
uspto-grants-2012_08
Patent number
US08236807B2

Linked notes

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