Trifluoroacetic acid → HCID 66724598, compound

HRID 1875931Notes

Reaction equation

HRID 1875931 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]([CH3:17])[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: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 57476570HCID 57476570, compound

Product 1

HCID 66724598HCID 66724598, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-Dimethoxybenzyl)-6-methylquinoxalin-2-amine (0.84 g, 2.72 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 Na2CO3 (200 mL) was added to the red residue, which then precipitated a tan solid. The mixture was extracted extensively with DCM. The organic layer was dried over sodium sulfate, concentrated, and dried under vacuum to afford 6-methylquinoxalin-2-amine 2,2,2-trifluoroacetate (640 mg, 2.343 mmol, 86% yield).

Workup

  1. customSolvents were removed on the rotary evaporator
  2. additionSaturated aqueous Na2CO3 (200 mL) was added to the red residue, which
  3. customthen precipitated a tan 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-1429f028894a4d5bb9a39d07a2aaaf8c
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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