Ammonia → 3-Chloro-6,7-dimethyl-quinoxalin-2-ylamine

HRID 1025478Notes

Reaction equation

HRID 1025478 reaction equation
[Cl:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.C(=O)=O.[NH3:18]>C1COCC1>[Cl:1][C:2]1[C:11]([NH2:18])=[N:10][C:9]2[C:4]([N:3]=1)=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[CH:8]=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 280Carbon DioxideHCID 40926472,3-Dichloro-6,7-dimethylquinoxaline

Product 1

HCID 856592133-Chloro-6,7-dimethyl-quinoxalin-2-ylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dichloro-6,7-dimethyl-quinoxaline (30 g) in 300 mL of THF was cooled with dry-ice in a sealed vessel. Ammonia gas was added for 10 min, then the mixture was heated to 100° C. for 20 h. After removal of the solvent in vaccuo the residue was purified by flash chromatography to yield 14 g of the title compound. 1H-NMR (300 MHz, d6-DMSO): δ=7.43 (1H, s), 7.37 (1H, s), 7.00 (2H, s), 2.28 (6H, s) ppm.

Workup

  1. customAfter removal of the solvent in vaccuo the residue
  2. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ac1cc7516bbc4f06a12ba5cae3ed3853
Source dataset
uspto-grants-2014_05
Patent number
US08729082B2

Reaction notes

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