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

HRID 1896588Notes

Reaction equation

HRID 1896588 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-N1-(2-chloroethyl)-N1-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-54d8a538063145cfb24ea58f5bb74c48
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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