Dimethylformamide → 3-Bromo-6,7-dichloroquinoxalin-2-amine

HRID 1266135Notes

Reaction equation

HRID 1266135 reaction equation
[Br:1][C:2]1[C:11](Br)=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.C[N:16](C=O)C>>[Br:1][C:2]1[C:11]([NH2:16])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:14])=[C:7]([Cl:13])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 15418643HCID 15418643, compound

Product 1

HCID 117483793-Bromo-6,7-dichloroquinoxalin-2-amineYield 89%

Procedure

2,3-Dibromo-6,7-dichloro-quinoxaline (2.75 g, 7.7 mmol) was dissolved in DMF (50 mL). Anhydrous ammonia was bubbled into the solution. After 2 hours, DMF was removed in vacuo at 70° C. The residue was filtered through a pad of silica gel (one inch thick) eluted with ethyl acetate. After removal of the solvent in vacuo, the residue was recrystallized from acetone to give the desired 2-bromo-3-amino-6,7-dichloroquinoxaline as a white solid. (7.84 g, 89% yield): mp 232-4° C.; Rf=0.41, EtOAc:Hex (1:1); IR (KBr, cm−1) 3488, 3348, 1617, 1588, 1443, 1406, 1338, 1114, 1036, 965, 893, 867, 577, 557; 1H NMR (DMSO) δ 8.02 (s, 1H), 7.76 (s, 1H), 7.51 (broad s, 2H, NH2), 7.18 (s, 2H); 13C NMR (DMSO) δ 147.7, 136.7, 131.4, 129.0, 128.8, 124.4, 122.3, 121.9; MS (ACPI), m/z 291.8 (M−1)−; Anal. Calcd for C8H4N3BrCl2: C, 32.80; H, 1.38; N, 14.34. Found: C, 32.98; H, 1.43; N, 14.34.

Workup

  1. customAnhydrous ammonia was bubbled into the solution
  2. customDMF was removed in vacuo at 70° C
  3. filtrationThe residue was filtered through a pad of silica gel (one inch thick)
  4. washeluted with ethyl acetate
  5. customAfter removal of the solvent in vacuo
  6. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-1b8b4ed950b84e1eb43063ac7b5496ac
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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