Potassium Carbonate → 6-Bromo-1-methyl-1,2,3,4-tetrahydroquinoxaline

HRID 2178238Notes

Reaction equation

HRID 2178238 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([N:8]([CH2:10][CH2:11]Cl)[CH3:9])=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH3:9])[CH2:10][CH2:11][NH:13]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59418741HCID 59418741, compound

Product 1

HCID 594187386-Bromo-1-methyl-1,2,3,4-tetrahydroquinoxalineYield 101.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-N′-(2-chloroethyl)-N′-methylbenzene-1,2-diamine (25D) (0.611 g, 2.3 mmol) and K2CO3 (0.634 g, 4.6 mmol) in DMF (7 mL) was heated to 80° C. for 1 hour and then at 100° C. for 1.5 hours, cooled to rt, diluted with water and extracted with EtOAc. The organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 0.528 g (100%) of the desired product 6-bromo-1-methyl-1,2,3,4-tetrahydroquinoxaline (25E): 1H NMR (300 MHz, CDCl3) δ 6.72 (1H, dd), 6.56 (1H, d), 6.38 (1H, d), 3.74 (1H, bs), 3.47 (2H, t), 3.22 (2H, t), 2.82 (3H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b81ebc6309324aab83d726e766fa2979
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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