Ammonium Hydroxide → HCID 89781995, compound

HRID 1055864Notes

Reaction equation

HRID 1055864 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([Cl:13])[C:6](Cl)=[N:7]2.[NH4+:14].[OH-]>CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([Cl:13])[C:6]([NH2:14])=[N:7]2

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 337783211092286-00-4

Product 1

HCID 89781995HCID 89781995, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromo-2,3-dichloroquinoxaline (Leadgen Labs, Orange, Conn.; 2.00 g, 7.20 mmol) in 50 mL DMF at 0° C. was added NH4OH (30% NH3 in water; 18.68 ml, 144 mmol) dropwise via syringe. A thick solid formed. 2 mL DMF was added to promote stirring. The thick reaction was sealed and stirred for 2 h at RT. The reaction was diluted with 250 mL water and let stand overnight. In the morning, it was filtered and the solid was air dried, treated with silica gel and DCM, and concentrated in vacuo. The material was purified by silica gel chromatography using 0-50% EtOAc/hexane to separately provide 5-bromo-3-chloroquinoxalin-2-amine (0.510 g, 1.973 mmol, 27% yield) as a peach-colored solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.69-7.76 (1H, m), 7.43-7.61 (4H, m). m/z (ESI, +ve) 259.9 (M+H)+ and 8-bromo-3-chloroquinoxalin-2-amine (0.78 g, 3.02 mmol, 42% yield) as a solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94 (1H, dd, J=7.6, 1.4 Hz), 7.73-7.79 (1H, m), 7.61 (2H, br. s.), 7.30 (1H, t, J=7.9 Hz). m/z (ESI, +ve) 259.9 (M+H)+.

Workup

  1. customA thick solid formed
  2. customThe thick reaction
  3. customwas sealed
  4. stirringstirred for 2 h at RT
  5. filtrationIn the morning, it was filtered
  6. customdried
  7. additiontreated with silica gel and DCM
  8. concentrationconcentrated in vacuo
  9. customThe material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6135d9f12fe64be2869b303190f1b586
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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