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

HRID 2209121Notes

Reaction equation

HRID 2209121 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>[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

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59418741HCID 59418741, compound

Product 1

HCID 594187386-Bromo-1-methyl-1,2,3,4-tetrahydroquinoxalineYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-bromo-N1-(2-chloroethyl)-N1-methylbenzene-1,2-diamine 1 (3.1 g, 0.012 mol) was dissolved in DMF (6 ml), Potassium carbonate (3.3 g, 0.024 mol) was added. The reaction was stirred at 100° C. for 2 h. The mixture was partitioned between water and EtOAc (2×30 mL) The combined organic layers was concentrated and purified by flash chromatography eluted with EtOAc to give 1.9 g, (69.6%) of 6-bromo-1-methyl-1,2,3,4-tetrahydroquinoxaline. 1H NMR (300 MHz, DMSO-d6) δ 6.50-6.45 (m, 2H), 6.31 (d, J=8.2 Hz, 1H), 5.79 (s, 1H), 3.29 (s, 4H). 3.07 (t, J=2.4 Hz, 2H), 2.71 (s, 3H), LCMS-ESI+ (m/z): [M+H]+ calcd for C9H11BrN2:226.01; found 226.96.

Workup

  1. customThe mixture was partitioned between water and EtOAc (2×30 mL) The combined organic layers
  2. concentrationwas concentrated
  3. custompurified by flash chromatography
  4. washeluted with EtOAc

Sources & evidence

ORD record
ord-9f9cee0a08d843e09bf7615f3c290f7d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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