Methylglyoxal → HCID 19909256, compound

HRID 1534301Notes

Reaction equation

HRID 1534301 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[N+](C1C=CC(N)=C(N)C=1)([O-])=O.CC(C=O)=O.[BH4-].[Na+]>C(O)(=O)C.O>[CH3:1][CH:2]1[CH2:11][NH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[NH:3]1

Participants

7

Reactant 4

HCID 880MethylglyoxalHCID 824610HCID 824610, compoundHCID 4311764Sodium borohydrideHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 19909256HCID 19909256, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1 g 2-methyl-6-nitroquinoxaline synthesized by the method described in Coll. Czech. Chem. Comm. 30, 3106 (1965) from 4-nitro-1,2-diaminobenzene by reaction with methyl glyoxal was dissolved in 30 ml acetic acid. Sodium borohydride was added to this solution in small portions at +5° C. until the starting compound could no longer be detected in the solution by thin-layer chromatography. The solution was then diluted with 200 ml water and extracted twice with chloroform. The organic phase was washed with water and dried. After concentration to dryness, the residue was dissolved in acetone and precipitated with hydrochloric acid. The yield amounted to 0.6 g (58% of the theoretical). The melting point of the 1,2,3,4-tetrahydro-2-methyl-6-nitroquinoxaline thus obtained was 178° C.

Workup

  1. extractionextracted twice with chloroform
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationAfter concentration to dryness
  5. dissolutionthe residue was dissolved in acetone
  6. customprecipitated with hydrochloric acid

Sources & evidence

ORD record
ord-4ad0b749e21c4ff888f1890c78adb981
Source dataset
uspto-grants-1992_02
Patent number
US05089025

Reaction notes

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