Trifluoroacetic acid → 6-Methoxyquinoxalin-2-amine

HRID 1875904Notes

Reaction equation

HRID 1875904 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 (1H, s), 7.54-7.58 (1H, m), 7.25-7.29 (2H, m), 4.71 (2H, br. s.), 3.90 (3H, 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-70db91f8c9134722b0236d4e9e66f14a
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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