Trifluoroacetic acid → HCID 69241680, compound

HRID 1907576Notes

Reaction equation

HRID 1907576 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:16]([O:17][CH3:18])=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:19])[CH:13]=2)[N:8]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:6][C:7]1[C:16]([O:17][CH3:18])=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:19])[CH:13]=2)[N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69243286HCID 69243286, compound

Product 1

HCID 69241680HCID 69241680, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2,4-dimethoxybenzylamino)-3-methoxy-6-methylquinoxaline (4.48 g, 13.2 mmol), 30 ml of 50% trifluoroacetic acid in dichloromethane was added at room temperature. The resulting mixture was stirred at room temperature for 18 hours and concentrated under the reduced pressure to remove the solvent. The residue was neutralized with saturated sodium bicarbonate solution and then NaCl solution was added thereto. The product was extracted with dichloromethanee and the organic layer was dried over MgSO4. After concentration under the reduced pressure, the crude product was purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (3:1) mixture and concentration gave 2.01 g of the titled compound (yield, 81%).

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. additionNaCl solution was added
  4. extractionThe product was extracted with dichloromethanee
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationAfter concentration under the reduced pressure
  7. customthe crude product was purified by SiO2 column chromatography
  8. extractionExtraction of the residue
  9. concentrationwith a n-hexane:ethyl acetate (3:1) mixture and concentration

Sources & evidence

ORD record
ord-30150db9196a45d0a15c2c3957f6de25
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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