5-bromo-1,2 dihydro-2,2-dimethyl-6-(2-imidazolin-2-ylamino)-3-(4H)-quinoxalinone → HCID 15225709, compound

HRID 1614549Notes

Reaction equation

HRID 1614549 reaction equation
[Br:1][C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=O)[C:6]([CH3:19])([CH3:18])[NH:7]2>O1CCCC1>[Br:1][C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[NH:4][CH2:5][C:6]([CH3:19])([CH3:18])[NH:7]2

Participants

3

Reactant 1

HCID 152257155-bromo-1,2 dihydro-2,2-dimethyl-6-(2-imidazolin-2-ylamino)-3-(4H)-quinoxalinone

Product 1

HCID 15225709HCID 15225709, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-bromo-1,2-dihydro-2,2-dimethyl-6-(2-imidazolin-2-ylamino)-3-(4H)-quinoxalinone (150 mg, 0.45 mmol) and LiALH4 (17 mg, 0.45 mmol) in tetrahydrofuran (3 ml) is heated and maintained at a temperature of 50°-80° C. until the starting material is consumed. The mixture is cooled to 0° C., 2-3 drops of H2O is added and the mixture is filtered. The solution is concentrated in vacuo to yield a residue which is chromatographed on silica gel with CHCl3 : CH3OH saturated with NH3 (g) elution to produce the title compound.

Workup

  1. temperatureis heated
  2. temperaturemaintained at a temperature of 50°-80° C. until the starting material
  3. customis consumed
  4. addition2-3 drops of H2O is added
  5. filtrationthe mixture is filtered
  6. concentrationThe solution is concentrated in vacuo
  7. customto yield a residue which
  8. customis chromatographed on silica gel with CHCl3
  9. washCH3OH saturated with NH3 (g) elution

Sources & evidence

ORD record
ord-4b11abdaa5744cae8ae344110d4923ba
Source dataset
uspto-grants-1993_03
Patent number
US05198442

Reaction notes

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