Trifluoroacetic acid → 6-Methoxyquinoxalin-2-amine

HRID 250038Notes

Reaction equation

HRID 250038 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[N:8]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:6])[CH:16]=[N:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57476556N-(2,4-dimethoxybenzyl)-6-methoxyquinoxalin-2-amine

Product 1

HCID 120087376-Methoxyquinoxalin-2-amineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-Dimethoxybenzyl)-6-methoxyquinoxalin-2-amine (2.8 g, 8.61 mmol) was stirred in TFA (10 mL, 130 mmol) and dichloromethane (10 mL) at ambient temperature for 30 min. The solvents were removed in vacuo. Saturated aq. sodium hydrogen carbonate (200 mL) was added to the red residue, which then precipitated a yellow solid. The mixture was extracted extensively with dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford 6-methoxyquinoxalin-2-amine (1.50 g, 8.56 mmol, 99% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.27 (1 H, s), 7.54-7.58 (1 H, m), 7.25-7.29 (2 H, m), 4.71 (2 H, br. s.), 3.90 (3 H, s). MS (LC/MS) R.T.=0.86; [M+H]+=176.23.

Workup

  1. customThe solvents were removed in vacuo
  2. additionSaturated aq. sodium hydrogen carbonate (200 mL) was added to the red residue, which
  3. customthen precipitated a yellow solid
  4. extractionThe mixture was extracted extensively with dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-306fae5eaf834d4c93ea4c03716ed897
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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