Trifluoroacetic acid → 7-Methoxyquinoxalin-2-amine 2,2,2-trifluoroacetate

HRID 250062Notes

Reaction equation

HRID 250062 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[N:8]=1.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>C(Cl)Cl>[F:28][C:27]([F:30])([F:29])[C:25]([OH:31])=[O:26].[CH3:18][O:17][C:11]1[CH:10]=[C:9]2[C:14]([N:15]=[CH:16][C:7]([NH2:6])=[N:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57476568N-(2,4-dimethoxybenzyl)-7-methoxyquinoxalin-2-amine

Product 1

HCID 667246317-Methoxyquinoxalin-2-amine 2,2,2-trifluoroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-Dimethoxybenzyl)-7-methoxyquinoxalin-2-amine (0.79 g, 2.428 mmol) was stirred in TFA (10 mL, 130 mmol)/CH2Cl2 (10 mL) at room temperature for 30 min. Solvents were removed on the rotary evaporator. Saturated aqueous NaHCO3 (200 mL) was added to the red residue, which precipitated a yellow solid. The mixture was extracted extensively with DCM. The organic layer was concentrated and dried under vacuum to yield 7-methoxyquinoxalin-2-amine 2,2,2-trifluoroacetate (0.70 g, 2.4 mmol, 99% yield).

Workup

  1. customSolvents were removed on the rotary evaporator
  2. additionSaturated aqueous NaHCO3 (200 mL) was added to the red residue, which
  3. customprecipitated a yellow solid
  4. extractionThe mixture was extracted extensively with DCM
  5. concentrationThe organic layer was concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-02c24e9977d54da7b8aacbb817c07191
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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