Trifluoroacetic acid → HCID 66724616, compound

HRID 1875934Notes

Reaction equation

HRID 1875934 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]([CH3:17])=[CH:12][CH:13]=2)[N:8]=1.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[CH3:17][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 57476572HCID 57476572, compound

Product 1

HCID 66724616HCID 66724616, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-Dimethoxybenzyl)-7-methylquinoxalin-2-amine (0.85 g, 2.75 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 then precipitated a pink solid. The mixture was extracted extensively with DCM. The organic layer was dried over sodium sulfate, concentrated, and dried under vacuum to afford 7-methylquinoxalin-2-amine 2,2,2-trifluoroacetate (640 mg, 2.34 mmol, 85% yield).

Workup

  1. customSolvents were removed on the rotary evaporator
  2. additionSaturated aqueous NaHCO3 (200 mL) was added to the red residue, which
  3. customthen precipitated a pink solid
  4. extractionThe mixture was extracted extensively with DCM
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9d2c79bbd1e0473daafbcd893617c32d
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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