Triethylamine → Ethyl 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 240346Notes

Reaction equation

HRID 240346 reaction equation
[O:1]=[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:17][C:18]#[CH:19].Cl[CH2:21][CH:22]=[N:23][OH:24].C(N(CC)CC)C>O1CCCC1>[CH3:21][C:22]1[CH:19]=[C:18]([CH2:17][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]2=[O:1])[O:24][N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57350373N-(2-Chloroethylidene)hydroxylamineHCID 86643865Ethyl 2-oxo-1-(2-propynyl)-1,2-dihydroquinoxaline-3-carboxylate

Product 1

HCID 67533297Ethyl 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (11.7 mmol) of ethyl 2-oxo-1-(2-propynyl)-1,2-dihydroquinoxaline-3-carboxylate and 3.28 g (35.1 mmol) of chloroacetaldoxime were dissolved in tetrahydrofuran (30 mL), and 3.55 g (35.1 mmol) of triethylamine was added dropwise at a temperature in the range of 0° C. to 5° C. The mixture was stirred for 3 days at room temperature. After confirming the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of citric acid, dried over anhydrous sodium sulfate, and concentrated. The solid matter thus obtained was washed with diisopropyl ether, to obtain 3.4 g (yield: 93%) of ethyl 1-[(3-methylisoxazol-5-yl)methyl]-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a white powder.

Workup

  1. customthe completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of citric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe solid matter thus obtained
  8. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-7560e989507a4381829699797f425804
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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