Oxalyl chloride → 1-Methyl-1,4-dihydro-2,3-quinoxalinedione

HRID 2291263Notes

Reaction equation

HRID 2291263 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][NH:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:7][N:8]1[C:9]2[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:11][C:2](=[O:3])[C:1]1=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 6006271-Methyl-1,4-dihydro-2,3-quinoxalinedione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 12 g of 98% oxalylchloride in 19.5 ml of triethylamine and 50 ml of toluene was added dropwise to a stirred solution of 8.5 g of o-N-methylamino aniline in 80 ml of toluene. The resulting mixture was heated at reflux for one hour. The precipitate was washed with ether. The residue was stirred with water and filtered to give 1,2,3,4-tetrahydro-1-methyl-2,3-dioxo-quinoxaline.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for one hour
  3. washThe precipitate was washed with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0efc13f43e24494ebec48300e42c4e6b
Source dataset
uspto-grants-1989_01
Patent number
US04795749

Reaction notes

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