Hydrogen Bromide → 1-(6-Methylpyridin-2-yl)-2-(quinoxalin-6-yl)ethane-1,2-dione

HRID 1071575Notes

Reaction equation

HRID 1071575 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])[CH:5]=[CH:4][CH:3]=1.Br.C([O-])([O-])=[O:23].[K+].[K+]>CS(C)=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8](=[O:23])[C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 223945292-(6-Methylpyridin-2-yl)-1-(quinoxalin-6-yl)ethanone

Product 1

HCID 223945261-(6-Methylpyridin-2-yl)-2-(quinoxalin-6-yl)ethane-1,2-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred suspension of 6-(2-[6-methylpyridin-2-yl]-acetyl)quinoxaline (1.65 g, 6.3 mmole) in dry DMSO (50 ml) was heated to 70-80° C. (forming a yellow solution) and treated dropwise with aq. HBr (48%, 6 ml). After 2 h the solution was cooled, poured over ice-water and brought to pH 10 with K2CO3. Extraction with EtOAc (3×), drying over Na2SO4, filtration and concentration to dryness in vacuo gave the title compound as a crimson oil (1.5 g, 86%). m/z [ESMS]: 278 [M+H]+.

Workup

  1. customforming a yellow solution) and
  2. temperatureAfter 2 h the solution was cooled
  3. extractionExtraction with EtOAc (3×)
  4. dry with materialdrying over Na2SO4, filtration and concentration to dryness in vacuo

Sources & evidence

ORD record
ord-77e653f553c4491b8d583a6a99198649
Source dataset
uspto-grants-2005_06
Patent number
US06906089B2

Reaction notes

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